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Sam Muchnick

Samuel Muchnick (born Jeshua Muchnick, August 22, 1905 – December 30, 1998 ) was an American professional wrestling promoter from St. Louis, Missouri. He is often regarded as wrestling's equivalent of Pete Rozelle (the forward-thinking commissioner who revolutionized the NFL), and he was instrumental in establishing the National Wrestling Alliance, which became the industry's top governing body, in 1948. Muchnick served as the NWA's president from 1950 to 1960 and again from 1963 to 1975. He operated the St. Louis Wrestling Club, one of the primary members of the NWA, based in St. Louis.

Early life
Muchnick was born in Ukraine to a Jewish family on August 22, 1905, but moved to the United States in 1911. He grew up in St. Louis, and his name was changed to Samuel when his father decided that Jeshua (Jesus or Joshua) was an inappropriate name for a Jewish child. While attending school, he worked various jobs to help out his family before earning his high school degree (though he ditched his graduation to attend a live wrestling event at the Odeon Theatre, where he watched the great Wladek Zbyszko in action). In 1924, he took a job with the U.S. Post Office; and in 1926, he joined the sports staff at the St. Louis Times newspaper, where he covered the St. Louis Cardinals baseball team while developing many influential acquaintances (including Babe Ruth, Al Capone, and others). Muchnick also covered professional wrestling, where he formed a friendship with Tom Packs, who was the Midwest's top sports promoter. In 1932, the Times merged with the rival St. Louis Star, and Muchnick left the paper for a position as Packs' publicist, where he handled public relations, finances and even booking duties.

St. Louis promoter
For nine years, Muchnick served as Tom Packs' righthand man while learning the ropes under one of the nation's most powerful promoters. However, Muchnick was insulted when Packs awarded him a paltry $200 bonus following the duo's successful promotion of the Joe Louis vs. Tony Musto heavyweight title bout in April 1941 (a fight that drew profits of $14,000). Muchnick then decided to leave his mentor when longtime wrestling champion Jim Londos (who was also on the outs with Packs) convinced him to start his own organization. Despite facing heavy resistance from Packs (who possessed much political clout with the State Athletic Commission), Muchnick promoted his first shows in May 1942 before enlisting in the Air Force during World War II. Upon returning, Muchnick continued to face competitive pressures from Packs; though he filed several court injunctions to promote his first show at St. Louis' renowned Kiel Auditorium on December 5, 1945. With the help of maverick Ohio promoter Jack Pfefer (who sent Sam several wrestlers to help him get started), Muchnick drew 3,771 fans to the arena while featuring such veteran wrestling stars as Ed "Strangler" Lewis, Roy Dunn, and others.

National Wrestling Alliance
Over the next few years, Muchnick was often forced to use old-timers past their primes as Packs employed most of the top talent (including reigning World Champion Lou Thesz). Then, in mid-1948, Muchnick was approached by Iowa's Pinky George and Minnesota's Tony Stecher about forming a new wrestling union. Up until this time, all pro wrestling regulations had come from the National Wrestling Association, which was made up of various athletic commissions. Their idea was to form a coalition of promoters, which would then share the bookings of the World Champion and top wrestlers while also splitting the gate draws. As a result, on July 19, 1948, Muchnick met with fellow promoters Pinky George, Wally Karbo (representing Tony Stecher), Orville Brown, Max Clayton, and Al Haft at the President Hotel in Waterloo, Iowa to form what was named the National Wrestling Alliance. Pinky George was named the organization's first President while Orville Brown was subsequently recognized as the first NWA World Heavyweight Champion. Shortly thereafter, Muchnick became the beneficiary of talent exchanges with various territories that joined the NWA. As a result, he was then able to secure the services of an innovative young heel named "Nature Boy" Buddy Rogers, who had previously been wrestling in Jack Pfefer's Toledo, Ohio territory. Rogers' outspoken persona and charismatic personality allowed him to outdraw even the great Lou Thesz (who by now had taken over much of Tom Packs' operation) while adding legitimacy to Muchnick's company. Eventually, the two St. Louis groups would merge while starting a promotional war angle; Muchnick kept a controlling interest in the territory by holding two percentage points more than Thesz. Then, on November 27, 1949, Thesz unified the National Wrestling Association and National Wrestling Alliance World Titles after Brown was injured in an auto accident prior to their scheduled match.

NWA President
In 1950, Sam Muchnick was named the new president of the NWA, a position to which he was unanimously re-elected for the next nine years due to the immense trust that he inspired among the various members of the organization. With Muchnick at the helm, the NWA became the dominant governing body in pro wrestling, as nearly every major wrestling territory across the country joined the Alliance in order to gain access to the treasure chest that was the NWA World Heavyweight Champion, who was universally recognized as the industry's premier star. Under Muchnick's leadership, the NWA would also donate thousands of dollars to help fund the U.S. Olympic Wrestling Team. Then, in the late 1950s, Sam Muchnick formed the St. Louis Wrestling Club while producing a new television program titled Wrestling at the Chase on KPLR-TV, which ran from May 23, 1959, to Sept. 10, 1983. There were approximately 1,100 episodes made during that time span. The show would become one of the most popular local productions in St. Louis television history, as it turned pro wrestling into a nationally popular entertainment while bringing the many stars of the NWA into the homes of its fans.

By 1960, Sam Muchnick stepped aside as NWA president so that the organization could benefit from new ideas. He served as executive secretary under Frank Tunney, Fred Kohler and Karl "Doc" Sarpolis. Consequently, Muchnick was unanimously re-installed as NWA president in 1963 and held the office until 1975, thus contributing a total of 25 years as the industry's most influential promoter. During his second reign, Muchnick maintained the NWA's position as wrestling's top power while he also displayed an uncanny eye for scouting future talent, as his St. Louis territory groomed such eventual champions as Johnny Valentine, Gene Kiniski, Harley Race, Dory Funk Jr., Terry Funk, Ric Flair, and many others. Moreover, he expanded the NWA globally by inking agreements with territories in Mexico, the Far East, Europe, and the Caribbean.

Retirement
Muchnick promoted his last card on January 1, 1982, which was subsequently named "Sam Muchnick Day" in St. Louis by Mayor Vincent Schoemehl. Shortly afterward, the St. Louis Wrestling Club was purchased by Bob Geigel, Pat O'Connor and Harley Race. Muchnick's former announcer and general manager Larry Matysik formed his own competing promotion in St. Louis around the same time. A year later, the WWF made a deal with Matysik which brought them into St. Louis and gave them the former TV timeslot of "Wrestling at the Chase." In 1985, the St. Louis Wrestling Club was sold to Jim Crockett Jr. and absorbed into what eventually became World Championship Wrestling. In 1990, he spoke at the beginning of WCW’s Starrcade. In 1997, during the World Wrestling Federation’s Badd Blood: In Your House pay-per-view, he was honored as a St. Louis legend.

Death
Muchnick died on December 30, 1998, in St. Louis. He was 93.

Championships and accomplishments

 * National Wrestling Alliance
 * NWA Hall of Fame (Class of 2005)
 * St. Louis Wrestling Hall of Fame
 * (Class of 2007)
 * Professional Wrestling Hall of Fame and Museum
 * (Class of 2003)
 * Wrestling Observer Newsletter
 * Wrestling Observer Newsletter Hall of Fame (Class of 1996)

title: Sam Muchnick


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User talk:Ollisiren

Kallio Senior Secondary School of Performing Arts
Please don't copy and paste material from other websites. Copyright violations are not acceptable. RickK 09:17, Feb 3, 2005 (UTC)

license: Creative Commons - Attribution Share-Alike - https://creativecommons.org/licenses/by-sa/4.0/

title: User talk:Ollisiren


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Wintergreen

Wintergreen is a group of aromatic plants. The term wintergreen once commonly referred to plants that remain green (continue photosynthesis) throughout the winter. The term evergreen is now more commonly used for this characteristic.

Most species of the shrub genus Gaultheria demonstrate this characteristic and are called wintergreens in North America, the most common generally being the American wintergreen (Gaultheria procumbens). Wintergreens in the genus Gaultheria contain an aromatic compound, methyl salicylate, and are used as a mintlike flavoring.

Uses

The berries of most species can be eaten raw or used in pies.

Wintergreen is a common flavoring in American products ranging from chewing gum, mints, and candies to smokeless tobacco such as dipping tobacco (American "dip" snuff) and snus. It is a common flavoring for dental hygiene products such as mouthwash and toothpaste. It is often a component of root beer, which originated in the United States.

Wintergreen oil is an ingredient in some vegetable-oil based lubricants used in firearm maintenance. These products, sold under the names Seal1 and Frog Lube, are proprietary blends of vegetable oils intended to clean, lubricate and preserve the metal surfaces of firearms. They have the advantages over petroleum-based products of being non-toxic and biodegradable.

Artificial wintergreen oil, which is pure methyl salicylate, is used in microscopy because of its high refractive index. Natural wintergreen oil can be distinguished from artificial by gas chromatography (GC) and GC isotope ratio mass spectrometry analysis.

Oil

The Gaultheria species share the common characteristic of producing oil of wintergreen. Wintergreen oil is a pale yellow or pinkish fluid liquid that is strongly aromatic with a sweet, woody odor (components: methyl salicylate (about 98%), α-pinene, myrcene, delta-3-carene, limonene, 3,7-guaiadiene, and delta-cadinene) that gives such plants a distinctive "medicinal" smell whenever bruised. Salicylate sensitivity is a common adverse reaction to the methyl salicylate in oil of wintergreen; it can produce allergy-like symptoms or asthma.

Wintergreen essential oil is usually obtained by steam distillation of the leaves of the plant following maceration in warm water. Methyl salicylate is not present in the plant until formed by enzymatic action from a glycoside within the leaves as they are macerated in warm water. Oil of wintergreen is also manufactured from some species of birch, but these deciduous trees are not called wintergreens. Spiraea plants also contain methyl salicylate in large amounts and are used similarly to wintergreen. Wintergreen has a strong "minty" odor and flavor; however, the Gaultheria-genus plants are not true mints, which belong to the genus Mentha.

Wintergreen also is used in some perfumery applications and as a flavoring agent for toothpaste, chewing gum, soft drinks, confectionery, Listerine, and mint flavorings. Wintergreen is used for rust removal and degreasing of machinery and is particularly effective for breaking through sea water corrosion.

Toxicity of oil
One milliliter (20 drops) of wintergreen oil is equivalent to about 1860 mg of aspirin, or almost six regular-strength adult aspirin tablets.

Treatment is identical to the other salicylates. Early use of hemodialysis in conjunction with maximal supportive measures is encouraged in any significant ingestion of methyl salicylate.

title: Wintergreen


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1,3-Dipolar cycloaddition

The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were described in the late 19th century to the early 20th century, following the discovery of 1,3-dipoles. Mechanistic investigation and synthetic application were established in the 1960s, primarily through the work of Rolf Huisgen. Hence, the reaction is sometimes referred to as the Huisgen cycloaddition (this term is often used to specifically describe the 1,3-dipolar cycloaddition between an organic azide and an alkyne to generate 1,2,3-triazole). 1,3-dipolar cycloaddition is an important route to the regio- and stereoselective synthesis of five-membered heterocycles and their ring-opened acyclic derivatives. The dipolarophile is typically an alkene or alkyne, but can be other pi systems. When the dipolarophile is an alkyne, aromatic rings are generally produced.

Mechanistic overview
Originally two proposed mechanisms describe the 1,3-dipolar cycloaddition: first, the concerted pericyclic cycloaddition mechanism, proposed by Rolf Huisgen; and second, the stepwise mechanism involving a diradical intermediate, proposed by Firestone. After much debate, the former proposal is now generally accepted —the 1,3-dipole reacts with the dipolarophile in a concerted, often asynchronous, and symmetry-allowed π4s + π2s fashion through a thermal six-electron Huckel aromatic transition state. However, a few examples exist of a stepwise mechanism for the catalyst-free 1,3-dipolar cycloaddition reactions of thiocarbonyl ylides, and nitrile oxides

Pericyclic mechanism
Huisgen investigated a series of cycloadditions between the 1,3-dipolar diazo compounds and various dipolarophilic alkenes. The following observations support the concerted pericyclic mechanism, and refute the stepwise diradical or the stepwise polar pathway.

 * Substituent effects: Different substituents on the dipole do not exhibit a large effect on the cycloaddition rate, suggesting that the reaction does not involve a charge-separated intermediate.
 * Solvent effects: Solvent polarity has little effect on the cycloaddition rate, in line with the pericyclic mechanism where polarity does not change much in going from the reactants to the transition state.
 * Stereochemistry: 1,3-dipolar cycloadditions are always stereospecific with respect to the dipolarophile (i.e., cis-alkenes giving syn-products), supporting the concerted pericyclic mechanism in which two sigma bonds are formed simultaneously.
 * Thermodynamic parameters: 1,3-dipolar cycloadditions have an unusually large negative entropy of activation similar to that of the Diels-Alder reaction, suggesting that the transition state is highly ordered, which is a signature of concerted pericyclic reactions.

1,3-Dipole
A 1,3-dipole is an organic molecule that can be represented as either an allyl-type or a propargyl/allenyl-type zwitterionic octet/sextet structures. Both types of 1,3-dipoles share four electrons in the π-system over three atoms. The allyl-type is bent whereas the propargyl/allenyl-type is linear in geometry. 1,3-Dipoles containing higher-row elements such as sulfur or phosphorus are also known, but are utilized less routinely.

Resonance structures can be drawn to delocalize both negative and positive charges onto any terminus of a 1,3-dipole (see the scheme below). A more accurate method to describe the electronic distribution on a 1,3-dipole is to assign the major resonance contributor based on experimental or theoretical data, such as dipole moment measurements or computations. For example, diazomethane bears the largest negative character at the terminal nitrogen atom, while hydrazoic acid bears the largest negative character at the internal nitrogen atom.

Consequently, this ambivalence means that the ends of a 1,3-dipole can be treated as both nucleophilic and electrophilic at the same time. The extent of nucleophilicity and electrophilicity at each end can be evaluated using the frontier molecular orbitals, which can be obtained computationally. In general, the atom that carries the largest orbital coefficient in the HOMO acts as the nucleophile, whereas that in the LUMO acts as the electrophile. The most nucleophilic atom is usually, but not always, the most electron-rich atom. In 1,3-dipolar cycloadditions, identity of the dipole-dipolarophile pair determines whether the HOMO or the LUMO character of the 1,3-dipole will dominate (see discussion on frontier molecular orbitals below).

Dipolarophile
The most commonly used dipolarophiles are alkenes and alkynes. Heteroatom-containing dipolarophiles such as carbonyls and imines can also undergo 1,3-dipolar cycloaddition. Other examples of dipolarophiles include fullerenes and nanotubes, which can undergo 1,3-dipolar cycloaddition with azomethine ylide in the Prato reaction.

Solvent effects
1,3-Dipolar cycloadditions experience very little solvent effect because both the reactants and the transition states are generally non-polar. For example, the rate of reaction between phenyl diazomethane and ethyl acrylate or norbornene (see scheme below) changes only slightly upon varying solvents from cyclohexane to methanol.

Lack of solvent effects in 1,3-dipolar cycloaddition is clearly demonstrated in the reaction between enamines and dimethyl diazomalonate (see scheme below). The polar reaction, N-cyclopentenyl pyrrolidine nucleophilic addition to the diazo compound, proceeds 1,500 times faster in polar DMSO than in non-polar decalin. On the other hand, a close analog of this reaction, N-cyclohexenyl pyrrolidine 1,3-dipolar cycloaddition to dimethyl diazomalonate, is sped up only 41-fold in DMSO relative to decalin.

Frontier molecular orbital theory

1,3-Dipolar cycloadditions are pericyclic reactions, which obey the Dewar-Zimmerman rules and the Woodward–Hoffmann rules. In the Dewar-Zimmerman treatment, the reaction proceeds through a 5-center, zero-node, 6-electron Huckel transition state for this particular molecular orbital diagram. However, each orbital can be randomly assigned a sign to arrive at the same result. In the Woodward–Hoffmann treatment, frontier molecular orbitals (FMO) of the 1,3-dipole and the dipolarophile overlap in the symmetry-allowed π4s + π2s manner. Such orbital overlap can be achieved in three ways: type I, II and III. The dominant pathway is the one which possesses the smallest HOMO-LUMO energy gap.

Type I
The dipole has a high-lying HOMO which overlaps with LUMO of the dipolarophile. A dipole of this class is referred to as a HOMO-controlled dipole or a nucleophilic dipole, which includes azomethine ylide, carbonyl ylide, nitrile ylide, azomethine imine, carbonyl imine and diazoalkane. These dipoles add to electrophilic alkenes readily. Electron-withdrawing groups (EWG) on the dipolarophile would accelerate the reaction by lowering the LUMO, while electron-donating groups (EDG) would decelerate the reaction by raising the HOMO. For example, the reactivity scale of diazomethane against a series of dipolarophiles is shown in the scheme below. Diazomethane reacts with the electron-poor ethyl acrylate more than a million times faster than the electron rich butyl vinyl ether.

This type resembles the normal-electron-demand Diels-Alder reaction, in which the diene HOMO combines with the dienophile LUMO.

Type II
HOMO of the dipole can pair with LUMO of the dipolarophile; alternatively, HOMO of the dipolarophile can pair with LUMO of the dipole. This two-way interaction arises because the energy gap in either direction is similar. A dipole of this class is referred to as a HOMO-LUMO-controlled dipole or an ambiphilic dipole, which includes nitrile imide, nitrone, carbonyl oxide, nitrile oxide, and azide. Any substituent on the dipolarophile would accelerate the reaction by lowering the energy gap between the two interacting orbitals; i.e., an EWG would lower the LUMO while an EDG would raise the HOMO. For example, azides react with various electron-rich and electron-poor dipolarophile with similar reactivities (see reactivity scale below).

Type III
The dipole has a low-lying LUMO which overlaps with HOMO of the dipolarophile (indicated by red dashed lines in the diagram). A dipole of this class is referred to as a LUMO-controlled dipole or an electrophilic dipole, which includes nitrous oxide and ozone. EWGs on the dipolarophile decelerate the reaction, while EDGs accelerate the reaction. For example, ozone reacts with the electron-rich 2-methylpropene about 100,000 times faster than the electron-poor tetrachloroethene (see reactivity scale below).

This type resembles the inverse electron-demand Diels-Alder reaction, in which the diene LUMO combines with the dienophile HOMO.

Reactivity
Concerted processes such as the 1,3-cycloaddition require a highly ordered transition state (high negative entropy of activation) and only moderate enthalpy requirements. Using competition reaction experiments, relative rates of addition for different cycloaddition reactions have been found to offer general findings on factors in reactivity.

 * Conjugation, especially with aromatic groups, increases the rate of reaction by stabilization of the transition state. During the transition, the two sigma bonds are being formed at different rates, which may generate partial charges in the transition state that can be stabilized by charge distribution into conjugated substituents.
 * More polarizable dipolarophiles are more reactive because diffuse electron clouds are better suited to initiate the flow of electrons.
 * Dipolarophiles with high angular strain are more reactive due to increased energy of the ground state.
 * Increased steric hindrance in the transition state as a result of unhindered reactants dramatically lowers the reaction rate.
 * Hetero-dipolarophiles add more slowly, if at all, compared to C,C-diapolarophiles due to a lower gain in sigma bond energy to offset the loss of a pi bond during the transition state.
 * Isomerism of the dipolarophile affects reaction rate due to sterics. trans-isomers are more reactive (trans-stilbene will add diphenyl(nitrile imide) 27 times faster than cis-stilbene) because during the reaction, the 120° bond angle shrinks to 109°, bringing eclipsing cis-substituents towards each other for increased steric clash.
 * Steric clash of dipolarophile substituents during 1,3-cycloaddition.png

Stereospecificity
1,3-dipolar cycloadditions usually result in retention of configuration with respect to both the 1,3-dipole and the dipolarophile. Such high degree of stereospecificity is a strong support for the concerted over the stepwise reaction mechanisms. As mentioned before, many examples show that the reactions were stepwise, thus, presenting partial or no stereospecificity.

With respect to dipolarophile
cis-Substituents on the dipolarophilic alkene end up cis, and trans-substituents end up trans in the resulting five-membered cyclic compound (see scheme below).

With respect to dipole
Generally, the stereochemistry of the dipole is not of major concern because only few dipoles could form stereogenic centers, and resonance structures allow bond rotation which scrambles the stereochemistry. However, the study of azomethine ylides has verified that cycloaddition is also stereospecific with respect to the dipole component. Diastereopure azomethine ylides are generated by electrocyclic ring opening of aziridines, and then rapidly trapped with strong dipolarophiles before bond rotation can take place (see scheme below). If weaker dipolarophiles are used, bonds in the dipole have the chance to rotate, resulting in impaired cycloaddition stereospecificity.

These results altogether confirm that 1,3-dipolar cycloaddition is stereospecific, giving retention of both the 1,3-dipole and the dipolarophile.

Diastereoselectivity
When two or more stereocenters are generated during the reaction, diastereomeric transition states and products can be obtained. In the Diels-Alder cycloaddition, the endo diastereoselectivity due to secondary orbital interactions is usually observed. In 1,3-dipolar cycloadditions, however, two forces influence the diastereoselectivity: the attractive π-interaction (resembling secondary orbital interactions in the Diels-Alder cycloaddition) and the repulsive steric interaction. Unfortunately, these two forces often cancel each other, causing poor diastereoselection in 1,3-dipolar cycloaddition.

Examples of substrate-controlled diastereoselective 1,3-dipolar cycloadditions are shown below. First is the reaction between and methyl acrylate. In the transition state, the phenyl and the methyl ester groups stack to give the cis-substitution as the exclusive final pyrroline product. This favorable π-interaction offsets the steric repulsion between the phenyl and the methyl ester groups. Second is the reaction between nitrone and dihydrofuran. The exo-selectivity is achieved to minimize steric repulsion. Last is the intramolecular azomethine ylide reaction with alkene. The diastereoselectivity is controlled by the formation of a less strained cis-fused ring system.

Directed 1,3-dipolar cycloaddition
Trajectory of the cycloaddition can be controlled to achieve a diastereoselective reaction. For example, metals can chelate to the dipolarophile and the incoming dipole and direct the cycloaddition selectively on one face. The example below shows addition of nitrile oxide to an enantiomerically pure allyl alcohol in the presence of a magnesium ion. The most stable conformation of the alkene places the hydroxyl group above the plane of the alkene. The magnesium then chelates to the hydroxyl group and the oxygen atom of nitrile oxide. The cycloaddition thus comes from the top face selectively.

Such diastereodirection has been applied in the synthesis of epothilones.

Regioselectivity
For asymmetric dipole-dipolarophile pairs, two regioisomeric products are possible. Both electronic/stereoelectronic and steric factors contribute to the regioselectivity of 1,3-dipolar cycloadditions.

Electronic/stereoelectronic effect
The dominant electronic interaction is the combination between the largest HOMO and the largest LUMO. Therefore, regioselectivity is governed by the atoms that bear the largest orbital HOMO and LUMO coefficients.

For example, consider the cycloaddition of diazomethane to three dipolarophiles: methyl acrylate, styrene or methyl cinnamate. The carbon of diazomethane bears the largest HOMO, while the end olefinic carbons of methyl acrylate and styrene bear the largest LUMO. Hence, cycloaddition gives the substitution at the C-3 position regioselectively. For methyl cinnamate, the two substituents (Ph v.s. COOMe) compete at withdrawing electrons from the alkene. The carboxyl is the better electron-withdrawing group, causing the β-carbon to be most electrophilic. Thus, cycloaddition yields the carboxyl group on C-3 and the phenyl group on C-4 regioselectively.

Steric effect
Steric effects can either cooperate or compete with the aforementioned electronic effects. Sometimes steric effects completely outweighs the electronic preference, giving the opposite regioisomer exclusively.

For example, diazomethane generally adds to methyl acrylate to give 3-carboxyl pyrazoline. However, by putting more steric demands into the system, we start to observe the isomeric 4-carboxyl pyrazolines. The ratio of these two regioisomers depends on the steric demands. At the extreme, increasing the size from hydrogen to t-butyl shifts the regioselectivity from 100% 3-carboxyl to 100% 4-carboxyl substitution.

Synthetic applications
1,3-dipolar cycloadditions are important ways toward the synthesis of many important 5-membered heterocycles such as triazoles, furans, isoxazoles, pyrrolidines, and others. Additionally, some cycloadducts can be cleaved to reveal the linear skeleton, providing another route toward the synthesis of aliphatic compounds. These reactions are tremendously useful also because they are stereospecific, diastereoselective and regioselective. Several examples are provided below.

Nitrile oxides
1,3-dipolar cycloaddition with nitrile oxides is a widely used masked-aldol reaction. Cycloaddition between a nitrile oxide and an alkene yields the cyclic isoxazoline product, whereas the reaction with an alkyne yields the isoxazole. Both isoxazolines and isoxazoles can be cleaved by hydrogenation to reveal aldol-type β-hydroxycarbonyl or Claisen-type β-dicarbonyl products, respectively.

Nitrile oxide-alkyne cycloaddition followed by hydrogenation was utilized in the synthesis of Miyakolide as illustrated in the figure below.

Carbonyl ylides
1,3-dipolar cycloaddition reactions have emerged as powerful tools in the synthesis of complex cyclic scaffolds and molecules for medicinal, biological, and mechanistic studies. Among them, [3+2] cycloaddition reactions involving carbonyl ylides have extensively been employed to generate oxygen-containing five-membered cyclic molecules.

Preparation of carbonyl ylides for 1,3-dipolar cycloaddition reactions
Ylides are regarded as positively charged heteroatoms connected to negatively charged carbon atoms, which include ylides of sulfonium, thiocarbonyl, oxonium, nitrogen, and carbonyl. Several methods exist for generating carbonyl ylides, which are necessary intermediates for generating oxygen-containing five-membered ring structures, for [3+2] cycloaddition reactions.

Synthesis of carbonyl ylides from diazomethane derivatives by photocatalysis
One of the earliest examples of carbonyl ylide synthesis involves photocatalysis. Photolysis of diazotetrakis(trifluoromethyl)cyclopentadiene* (DTTC) in the presence of tetramethylurea can generate the carbonyl ylide by an intermolecular nucleophilic attack and subsequent aromatization of the DTTC moiety. This was isolated and characterized by X-ray crystallography due to the stability imparted by aromaticity, electron withdrawing trifluoromethyl groups, and the electron donating dimethylamine groups. Stable carbonyl ylide dipoles can then be used in [3+2] cycloaddition reactions with dipolarophiles.

Another early example of carbonyl ylide synthesis by photocatalysis was reported by Olah et al. Dideuteriodiazomethane was photolysed in the presence of formaldehyde to generate the dideuterioformaldehyde carbonyl ylide.

Synthesis of carbonyl ylides from hydroxypyrones by proton transfer
Carbonyl ylides can be synthesized by acid catalysis of hydroxy-3-pyrones in the absence of a metal catalyst. An initial tautomerization occurs, followed by elimination of the leaving group to aromatize the pyrone ring and to generate the carbonyl ylide. A cycloaddition reaction with a dipolarophile lastly forms the oxacycle. This approach is less widely employed due to its limited utility and requirement for pyrone skeletons.

5-hydroxy-4-pyrones can also be used to synthesize carbonyl ylides by an intramolecular hydrogen transfer. After hydrogen transfer, the carbonyl ylide can then react with dipolarophiles to form oxygen-containing rings.

Synthesis of α-halocarbonyl ylides from dihalocarbenes
Dihalocarbenes have also been employed to generate carbonyl ylides, exploiting the electron withdrawing nature of dihalocarbenes. Both phenyl(trichloromethyl)mercury and phenyl(tribromomethyl)mercury are sources dichlorocarbenes and dibromocarbenes, respectively. The carbonyl ylide can be generated upon reaction of the dihalocarbenes with ketones or aldehydes. However, the synthesis of α-halocarbonyl ylides can also undesirably lead to the loss of carbon monoxide and the generation of the deoxygenation product.

Synthesis of carbonyl ylides from diazomethane derivatives by metal catalysis
A universal approach for generating carbonyl ylides involves metal catalysis of α-diazocarbonyl compounds, generally in the presence of dicopper or dirhodium catalysts. After release of nitrogen gas and conversion to the metallocarbene, an intermolecular reaction with a carbonyl group can generate the carbonyl ylide. Subsequent cycloaddition reaction with an alkene or alkyne dipolarophile can afford oxygen-containing five-membered rings. Popular catalysts that give modest yields towards synthesizing oxacycles include Rh2(OAc)4 and Cu(acac)2.

Mechanism of the 1,3-dipolar cycloaddition reaction mediated by metal catalysis of diazocarbonyl compounds
The universality and extensive use of 1,3-dipolar cycloaddition reactions mediated by metal catalysis of diazocarbonyl molecules, for synthesizing oxygen-containing five-membered rings, has spurred significant interest into its mechanism. Several groups have investigated the mechanism to expand the scope of synthetic molecules with respect to regio- and stereo-selectivity. However, due to the high turn over frequencies of these reactions, the intermediates and mechanism remains elusive. The generally accepted mechanism, developed by characterization of stable ruthenium-carbenoid complexes and rhodium metallocarbenes, involves an initial formation of a metal-carbenoid complex from the diazo compound. Elimination of nitrogen gas then affords a metallocarbene. An intramolecular nucleophilic attack by the carbonyl oxygen regenerates the metal catalyst and forms the carbonyl ylide. The carbonyl ylide can then react with an alkene or alkyne, such as dimethyl acetylenedicarboxylate (DMAD) to generate the oxacycle.

However, it is uncertain whether the metallocarbene intermediate generates the carbonyl ylide. In some cases, metallocarbenes can also react directly with dipolarophiles. In these cases, the metallocarbene, such as the dirhodium(II)tetracarboxylate carbene, is stabilized through hyperconjugative metal enolate-type interactions. Subsequent 1,3-dipolar cycloaddition reaction occurs through a transient metal-complexed carbonyl ylide. Therefore, a persistent metallocarbene can influence the stereoselectivity and regioselectivity of the 1,3-dipolar cycloaddition reaction based on the stereochemistry and size of the metal ligands.

The mechanism of the 1,3-dipolar cycloaddition reaction between the carbonyl ylide dipole and alkynyl or alkenyl dipolarophiles has been extensively investigated with respect to regioselectivity and stereoselectivity. As symmetric dipolarophiles have one orientation for cycloaddition, only one regioisomer, but multiple stereoisomers can be obtained. On the contrary, unsymmetric dipolarophiles can have multiple regioisomers and stereoisomers. These regioisomers and stereoisomers may be predicted based on frontier molecular orbital (FMO) theory, steric interactions, and stereoelectronic interactions.

Regioselectivity of the 1,3-dipolar cycloaddition reaction mediated by metal catalysis of diazocarbonyl compounds
Regioselectivity of 1,3-dipolar cycloaddition reactions between carbonyl ylide dipoles and alkynyl or alkenyl dipolarophiles is essential for generating molecules with defined regiochemistry. FMO theory and analysis of the HOMO-LUMO energy gaps between the dipole and dipolarophile can rationalize and predict the regioselectivity of experimental outcomes. The HOMOs and LUMOs can belong to either the dipole or dipolarophile, for which HOMOdipole-LUMOdipolarophile or HOMOdipolarophile-LUMOdipole interactions can exist. Overlap of the orbitals with the largest coefficients can ultimately rationalize and predict results.

The archetypal regioselectivity of the 1,3-dipolar cycloaddition reaction mediated by carbonyl ylide dipoles has been examined by Padwa and coworkers. Using a Rh2(OAc)4 catalyst in benzene, diazodione underwent a 1,3-dipolar cycloaddition reaction with methyl propiolate and methyl propargyl ether. The reaction with methyl propiolate affords two regioisomers with the major resulting from the HOMOdipole-LUMOdipolarophile interaction, which has the largest coefficients on the carbon proximal to the carbonyl group of the carbonyl ylide and on the methyl propiolate terminal alkyne carbon. The reaction with methyl propargyl ether affords one regioisomer resulting from the HOMOdipolarophile-LUMOdipole interaction, which has largest coefficients on the carbon distal to the carbonyl group of the carbonyl ylide and on the methyl propargyl ether terminal alkyne carbon.

Regioselectivities of 1,3-dipolar cycloaddition reactions mediated by metal catalysis of diazocarbonyl compounds may also be influenced by the metal through formation of stable metallocarbenes. Stabilization of the metallocarbene, via metal enolate-type interactions, will prevent the formation of carbonyl ylides, resulting in a direct reaction between the metallocarbene dipole and an alkynyl or alkenyl dipolarophile (see image of The dirhodium(II)tetracarboxylate metallocarbene stabilized by πC-Rh→πundefined hyperconjugation.). In this situation, the metal ligands will influence the regioselectivity and stereoselectivity of the 1,3-dipolar cycloaddition reaction.

Stereoselectivity and asymmetric induction of the 1,3-dipolar cycloaddition reaction mediated by metal catalysis of diazocarbonyl compounds
The stereoselectivity of 1,3-dipolar cycloaddition reactions between carbonyl ylide dipoles and alkenyl dipolarophiles has also been closely examined. For alkynyl dipolarophiles, stereoselectivity is not an issue as relatively planar sp2 carbons are formed, while regioselectivity must be considered (see image of the Products of the 1,3-Dipolar Cycloaddition Reaction Between Carbonyl Ylide Dipoles and Alkenyl or Alkynyl Dipolarophiles). However, for alkenyl dipolarophiles, both regioselectivity and stereoselectivity must be considered as sp3 carbons are generated in the product species.

1,3-dipolar cycloaddition reactions between carbonyl ylide dipoles and alkenyl dipolarophiles can generate diastereomeric products. The exo product is characterized with dipolarophile substituents being cis to the ether bridge of the oxacycle. The endo product is characterized with the dipolarophile substituents being trans to the ether bridge of the oxacycle. Both products can be generated through pericyclic transitions states involving concerted synchronous or concerted asynchronous processes.

One early example conferred stereoselectivity in terms of endo and exo products with metal catalysts and Lewis acids. Reactions with just the metal catalyst Rh2(OAc)4 prefer the exo product while reactions with the additional Lewis acid Yb(OTf)3 prefer the endo product. The endo selectivity observed for Lewis acid cycloaddition reactions is attributed to the optimized orbital overlap of the carbonyl π systems between the dipolarophile coordinated by Yb(Otf)3 (LUMO) and the dipole (HOMO). After many investigations, two primary approaches for influencing the stereoselectivity of carbonyl ylide cycloadditions have been developed that exploit the chirality of metal catalysts and Lewis acids.

The first approach employs chiral metal catalysts to modulate the endo and exo stereoselectivity. The chiral catalysts, in particular Rh2[(S)-DOSP]4 and Rh2[(S)-BPTV]4 can induce modest asymmetric induction and was used to synthesize the antifungal agent pseudolaric acid A. This is a result of the chiral metal catalyst remaining associated with the carbonyl ylide during the cycloaddition, which confers facial selectivity. However, the exact mechanisms are not yet fully understood.

The second approach employs a chiral Lewis acid catalyst to induce facial stereoselectivity after the generation of the carbonyl ylide using an achiral metal catalyst. The chiral Lewis acid catalyst is believed to coordinate to the dipolarophile, which lowers the LUMO of the dipolarophile while also leading to enantioselectivity.

Azomethine ylides
1,3-Dipolar cycloaddition between an azomethine ylide and an alkene furnishes an azacyclic structure, such as pyrrolidine. This strategy has been applied to the synthesis of spirotryprostatin A.

Ozone
Ozonolysis is a very important organic reaction. Alkenes and alkynes can be cleaved by ozonolysis to give aldehyde, ketone or carboxylic acid products.

Biological applications
The 1,3-dipolar cycloaddition between organic azides and terminal alkynes (i.e., the Huisgen cycloaddition) has been widely utilized for bioconjugation.

Copper catalysis
The Huisgen reaction generally does not proceed readily under mild conditions. Meldal et al. and Sharpless et al. independently developed a copper(I)-catalyzed version of the Huisgen reaction, CuAAC (for Copper-catalyzed Azide-Alkyne Cycloaddition), which proceeds very readily in mild, including physiological, conditions (neutral pH, room temperature and water solution). This reaction is also bioorthogonal: azides and alkynes are both generally absent from biological systems and therefore these functionalities can be chemoselectively reacted even in the cellular context. They also do not react with other functional groups found in nature, so they do not perturb biological systems. The reaction is so versatile that it is termed the "Click" chemistry. Although copper(I) is toxic, many protective ligands have been developed to both reduce cytotoxicity and improve rate of CuAAC, allowing it to be used in in vivo studies.

For example, Bertozzi et al. reported the metabolic incorporation of azide-functionalized saccharides into the glycan of the cell membrane, and subsequent labeling with fluorophore-alkyne conjugate. The result is that the cell membrane is fluorescently labeled, and can therefore be imaged using a fluorescence microscope.

Strain-promoted cycloaddition
To avoid toxicity of copper(I), Bertozzi et al. developed the strain-promoted azide-alkyne cycloaddition (SPAAC) between organic azide and strained cyclooctyne. The angle distortion of the cyclooctyne helps to speed up the reaction by both reducing the activation strain and enhancing the interactions, thereby enabling it to be used in physiological conditions without the need for the catalyst.

For instance, Ting et al. introduced an azido functionality onto specific proteins on the cell surface using a ligase enzyme. The azide-tagged protein is then labeled with cyclooctyne-fluorophore conjugate to yield a fluorescently labeled protein.

title: 1,3-Dipolar cycloaddition


text:
Buff arches

The buff arches (Habrosyne pyritoides) is a moth of the family Drepanidae. The species was first described by Johann Siegfried Hufnagel in 1766. It is found throughout Europe and is well distributed in the British Isles except the far north of England and all of Scotland. They live in deciduous and coniferous forests with large populations of their foodplants, but also in gardens and parks.

This is a distinctive and attractive species; its grey-brown forewings are marked with bold buff-orange "arches". The hindwings are grey with white margins. The wingspan is 40–45 mm. It flies from June to August and is attracted to light and sugar.

The young caterpillars are dark brown to grey-brown and more clearly spotted than the later caterpillar stages. These are brown-red and have a narrow dark dorsal line with indistinct light side spots. They have white spots on the sides of the three front abdominal segments, which become smaller to the rear, or just such a spot on the first abdominal segment. The larva feeds on bramble, hawthorn and hazel. The species overwinters as a pupa.

This moth is one of many insects that has been badly affected by light pollution with the species population declining by 62% since the 1970s.

 * 1)  The flight season refers to the British Isles. This may vary in other parts of the range.

Subspecies

 * Habrosyne pyritoides pyritoides (Europe, northern Iran)
 * Habrosyne pyritoides derasoides (Butler, 1878) (south-eastern Russia, Korean Peninsula, Japan, China: Heilongjiang, Jilin, Liaoning, Beijing, Hebei)

title: Buff arches


text: Category:Communes of Haute-Loire

title: Category:Communes of Haute-Loire


text:
Talk:List of collectible card games

Pirates of the Spanish Main
What definition of Collectible Card Games makes you so sure that PSM isn't a CCG? Wouter Lievens 09:25, 3 Feb 2005 (UTC)

 * The one that says "you play the game with cards". Punch-outs are not card games. -- Netoholic @ 15:42, 2005 Feb 3 (UTC)

 * Half of the game is about the cards. They contain the stats of the ships and the crew. There is also the aspect of secret cards because some crew and/or treasure can be hidden from other players. Also, the creators market it as a CCG. Wouter Lievens 18:11, 3 Feb 2005 (UTC)

 * Look at their rules section.  A lot of miniatures games (D&D comes to mind) have cards that display stats. They are not CCGs.  In this case, the creators package it somewhat like a CCG, and market it to the CCG crowd, but it is still not a CCG. -- Netoholic @ 18:26, 2005 Feb 3 (UTC)

 * Is Ani-Mayhem! a CCG? In what ways does its board-game-style position-based gameplay, which deviates from standard CCGs just as much as Pirates, include it but exclude Pirates? (see also: Talk:Pirates of the Spanish Main) --Boco XLVII 21:42, 3 Feb 2005 (UTC)

 * CCG's often use a special layout on the playing surface. Until the Ani-Mayhem! guys start cutting apart their cards and building little ships, though, this has nothing to do with Pirates. -- Netoholic @ 22:26, 2005 Feb 3 (UTC)

 * So your issue is with dimensionality of cards? M:tG Unglued has cards that require they be torn into pieces.  Does that make it not a CCG? (what I'm trying to get from you is a definition of CCG) --Boco XLVII 22:38, 3 Feb 2005 (UTC)

 * This conversation is honestly getting stupid. You want a definition, go read collectible card game - I wrote quite a bit of it. -- Netoholic @ 00:46, 2005 Feb 4 (UTC)

 * From that page I see that the only rule being violated is the lack of card drawing; all cards begin in play and can later be removed or re-added. About half of the cards in play are face-down, though, and those are randomly located - Explore is the equivalent of a Draw action.  Every other rule of being a CCG is followed.  I suggest you either improve the linked article (not to say it is poorly written, just to say that it is unclear on a definition of CCG, especially one in which this game is not included) or say something relevant. --Boco XLVII 04:52, 4 Feb 2005 (UTC)

The reason this is not a CCG is because this is a miniatures game. The game is played with miniatures. They are stored on cards, but the cards themselves hove no game value other than reference. Therefore, the game is no played with cards; it is not a CCG.

Dragon Storm

 * Dragon Storm (Black Dragon Press)

This is a role-playing game that uses cards extensively, but is not a collectible card game. The players make a big deal about that. -- Netoholic @ 07:21, 4 October 2005 (UTC)

Sounds a lot like a technicality or politics, but it is not a CCG as defined by the definition of a collectible card game, correct?

CC & SH Universe

 * CC & SH Universe (CC & SH Games)

No source information, I can find nothing about it. -- Netoholic @ 07:21, 4 October 2005 (UTC)

Final Fantasy

 * Final Fantasy IX: Tetra Master (Dino Entertainment/Square Europe)
 * Final Fantasy VIII: Triple Triad (Bandai)

As far as I can tell, these are card games, but non-collectible (sold as a set). -- Netoholic @ 07:44, 4 October 2005 (UTC)

Final Fantasy VIII is packaged in boosters of 10 cards each. Cards are numbered for collectibility. Final Fantasy VIII is not sold as a set, but Final Fantasy IX is.

Super Nova

 * Super Nova (Buccaneer Games)

Players draw off a shared deck of cards. -- Netoholic @ 07:44, 4 October 2005 (UTC)

This does not invalidate this game as being a CCG under the definition of a collectible card game. Nowhere in the definition does it say players have different decks. The game is packaged as a CCG, and is collectible in the same manner. Therefore, this should be a CCG by the current definition.

Battle Cards

 * Battle Cards (Steve Jackson Games/Merlin)

Mechanically not much like a CCG. Steve Jackson Games got a lot of ears talking about how this was out before Magic, but may be a bit of historical revisionism? Here is a gameplay description]. -- Netoholic @ 07:44, 4 October 2005 (UTC)

Cardmaster Conflict

 * Cardmaster Conflict

Someone's personal programming project. -- Netoholic @ 20:17, 8 December 2005 (UTC)

Sandwich Shop

 * Sandwich Shop (CCG Workshop LLC)

Not a notable commercial release. -- Netoholic @ 20:17, 8 December 2005 (UTC)

Top Trumps

 * Top Trumps (Winning Moves)

Shared deck, no more a CCG than UNO. -- Netoholic @ 20:17, 8 December 2005 (UTC)

Base Ball Card Game

 * Base Ball Card Game (The Allegheny Card Co.)

Need a source for the game rules, but likely a fantasy baseball variant. -- Netoholic @ 20:17, 8 December 2005 (UTC)

Topps FantaSports

 * Topps FantaSports (The Topps Company, Inc.)

Need a source for the game rules, but likely a fantasy football variant. -- Netoholic @ 10:07, 8 January 2006 (UTC)

Mystick: Domination

 * Mystick: Domination (Anoch Game Systems) (possibly non-collectible)

Mystick is a Customizable game, but comes in two set decks that you can mix. No collectibility on this game at all. -- Century

http://www.wuxiapian.com/ and http://www.animalherders.com/ links to some crap instead of actual CCG. spam?

Wakfu
This game does not appear to ever have been published in English. Siliconcrusader (talk) 05:01, 21 September 2015 (UTC)

Alteil

 * Alteil ||2004||?||No

Alteil is a DCCG --Squeezums (talk) 17:48, 4 November 2019 (UTC)
 * It may have been a DCCG, but the source provided showed a CCG as well. Leitmotiv (talk) 20:29, 4 November 2019 (UTC)
 * The archived source doesn't seem to indicate the game to be a physical card game, and the pictured cards are too low quality to determine if it is a picture of physical or digital cards. In researching for any supporting source, I have been unable to find any reference of a physical game aside from the game being listed in the (now defunct) source. Even the game's article calls Alteil an online CCG. Even if this game does exist in a physical format, I think a more concrete source has to be found before the game can be included in the list. --Squeezums (talk) 20:54, 4 November 2019 (UTC)

 * I've continued searching and found a store listing a booster pack. My apologies for posting so shortly before finding a hit. I will be updating the list reference with this new link although it is unfortunately not very descriptive of the game. Hopefully we can find another better reference in the future. --Squeezums (talk) 21:03, 4 November 2019 (UTC)

 * Yeah that source is not the best, but it was exhaustive - with pictures of the cards. I was never able to list all the CCGs they had on that website. I got to the letter C or D and stopped. They had a lot of Japanese CCGs, which will undoubtedly be much harder to verify in English speaking countries, such as mine. The site is defunct now, and to my knowledge, there's no way of pulling up the remaining ones I never got to listing on this article. And there were a lot! This list article would have easily doubled in size.

 * For the record, the photos at web archive, show a 9-card page holder for Alteil. I definitely see physical cards in a 9-card page holder, so definitely not DCCG per that archived source. I think Japan companies made a lot of quick one-offs as flavors of the year - so there is likely tons of these CCGs that aren't documented in English speaking countries. Leitmotiv (talk) 21:20, 4 November 2019 (UTC)

 * I've managed to find the archived homepage of the library used for so many of these sources. Thankfully, it seems like most of the library has been archived intact. I will put a link to the archived library right here (http://web.archive.org/web/20181105113929/http://www.geocities.jp/lib_gov/tcg/tcg_lib_index.html). I've tested a few random entries and all seem to have been archived completely. I am very optimistic that the entire library is archived safely. Hopefully we can work together to continue to pull more games onto this list.--Squeezums (talk) 22:43, 4 November 2019 (UTC)

 * Hey that's what I was trying to look for! Thanks very much. I thought it only archived the pages that Wikipedia had linked to around the time I did my 2018 updates. Glad to see that's not the case. It's a lot to work through, but I will eventually get to it with my other projects that are non-Wikipedia related. I believe the trouble I had before was determining which of these sets were core games and not just expansions of another core game. You see, there are some games that have a core game system that is referred to in a round about way, but the expansions appear as if they're their own thing, but instead all use the core gaming system and can be used with the other expansions. You will see this in the form of IPs, like the Street Fighter card game, or The SNK card game, but both use the same rules and can be used together under some core base game that has it's own separate name - and it is the core game that should receive the only mention, though it could have a footnote stating all the expansions. Leitmotiv (talk) 00:49, 5 November 2019 (UTC)

 * One more set of good news to share. I reached out to the owner of that site. It turns out, the owner did re-host the website at a different host. He said that he has not updated it recently, but he still plans to in the future. Here is the link to the un-archived, currently running webstite (http://libgov.starfree.jp/index.html). And here is the link directly to the TCG library (http://libgov.starfree.jp/tcg/tcg_lib_index.html). Given that resources can be hard to find for this subject (especially for Japanese games) should we potentially create a location at the top of the talk page for listing some of the really useful, but harder to find resources? -Squeezums (talk) 15:01, 5 November 2019 (UTC)

Other computer / console games as CCGs
I'm not sure if they're close enough to put on the list, but the following games are based at least partially on mechanics that closely resemble CCGs: 69.85.162.195 21:52, 31 December 2006 (UTC)
 * Etherlords
 * Etherlords 2
 * Metal Gear Acid
 * Metal Gear Acid 2
 * Phantasy Star Online Episode III C.A.R.D. Revolution
 * It's a very difficult line to draw. In some cases one has to make a distinction based on whether the game actually revolves around cards, or just uses cards as a mechanic.  For example, Baten Kaitos uses cards for item collection, for quests, and for combat.  Yet, the cards are just a mechanic, they're not actually the sole activity in the game.  Even so, there will undoubtedly be individuals with different opinions on the subject. -- Slordak 16:19, 9 January 2007 (UTC)

What exactly is considered an "actively supported" CCG?
There are only three games listed there, but there are still far far more in production, actively supporting and actively played, unless of course there are some set guidelines detailing exactly what "actively" means, but I do not see these anywhere on the page -- so, what exactly is an "actively supported" CCG? —The preceding unsigned comment was added by Josh7289 (talk • contribs) 00:32, 19 March 2007 (UTC).

 * That portion was removed from the page. While it is a good idea, it would have to be defined in order to be useful. -- Century

 * I think it would be useful, however, to note each game in the list that has been officially discontinued by the manufacturer. I'm not talking about making a separate section, but just a note or something by the name of each discontinued game.  I think something like this leaves no room for ambiguity, and could be pretty useful. —The preceding unsigned comment was added by Josh7289 (talk • contribs) 01:06, 20 March 2007 (UTC).

 * There are many games that have not been officially discontinued, but are obviously not being supported. It's hard to differentiate there.  Then again, there are CCGs like Buffy The Vampire Slayer that are supported by fans, but not the manufacturer. --Century 02:44, 20 March 2007 (UTC)

Garbage Pale Kids
Is there a known page for the "Garbage Pale Kids" collection? If so, why is it not on the list? —Preceding unsigned comment added by 68.1.28.249 (talk) 21:14, 6 September 2007 (UTC)

 * Are we talking about the old Garbage Pail Kids from the 1980s? If so, while collectible, they aren't used to actually play a game as defined in the primary article on the subject.  This list is a list of collectible card games, not a list of collectible cards (e.g. baseball cards) or collectible products in general. --Slordak 16:04, 7 September 2007 (UTC)

bobobo trading card game
there was also a not well known bobobo trading card game.I'll have a source up soon.

Alphabetical Listing
I added an alphabetical listing. I know nothing about Trading Card Games. My seven year old boy is interested, and I am trying to learn. The essential purpose of Wikipedia is to imform the ignorant. Those of us ignorant about Treding Card Games need an alphabetical listing, as the only thing we are likely to know is the name of the game.

Is there something about these games that invalidates my thinking? Nwbeeson 14:12, 18 June 2007 (UTC)

 * No, but the distinction between physical card games (games where one owns the actual pieces of card stock), virtual games (games where one "owns" virtual representations of cards), and video games which merely simulate this activity is very important. I would propose 3 separate sortable tables, one for each of these.  With both the release date and title included, one could then sort them as desired. --Slordak 14:16, 18 June 2007 (UTC)

 * I think alphabetical listings would be more useful than the current sortings, and I also agree that the three separate groups should be maintained. Once it's complete, I'd have the older lists removed, as otherwise it's just duplication of information. -masa ♫  15:11, 18 June 2007 (UTC)

Collectible vs. Collectable
Please note that there are two accepted spellings of this word and different companies have used different spellings. Please leave them as they are. --Century 23:32, 26 September 2007 (UTC)

Never released in USA
What about those Trading Card Games what hasn't been released in USA? --Szente (talk) 21:30, 17 May 2012 (UTC)

CCGs list as Sorted Table?
Wouldn't it be better to have the list of CCGs in a user-sortable table? This would remove the redundancy of having seperate alphabetical and date-sorted sections, and would make it easier to access the information. Thomasdav26 (talk) 20:21, 31 May 2013 (UTC)

resorting the T section
If no one objects, I'm going to resort the T section. Most the titles starting with "The" such as "The X-Files" should be relisted in their proper section, such a X for The X-Files. The new listing for the X-Files would read: "X-Files, The." When sorting alphabetically and the first word is "the" you should always alphabetize by the second word. Leitmotiv (talk) 06:03, 28 August 2013 (UTC)
 * Done. Leitmotiv (talk) 23:17, 28 August 2013 (UTC)

English language games only?
Should this list include games which have only been available in a foreign language or only games which are/were published in English? -- Siliconcrusader (talk) 05:13, 21 September 2015 (UTC)
 * Any language is fine, so long as you can verify through a language conversion site that it is indeed a CCG. Leitmotiv (talk) 15:21, 21 September 2015 (UTC)

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Where is the list of online collectible card games?
The article says to see the section near the bottom, but I can’t find the section described. Papí • talk 06:23, 19 June 2017 (UTC)

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PEZ Card Game
The references for this game are very week with the only non-wiki reference being the Scrye checklist. The description of the game seems to imply that the game is played with a shared deck rather than each player having their own deck. This deck does seems to be modified by blind booster packs, and the article does call the game a CCG so it may still qualify as a CCG. I'm not certain on the exact line drawn to define a CCG. --Squeezums (talk) 17:14, 4 November 2019 (UTC)
 * The quick answer to your questioning of Pez, is that it's not for us to decide what is and what isn't a CCG. The sources we provide do. The two Scrye guides are pretty much the bible for all CCGs up to 2003. They are also the ones that defined having a common deck versus a personal deck, and they reviewed Pez as being a CCG and not a common deck game ("shared deck" in your words). If you're interested in any of these CCGs cited by Scrye, I recommend picking up the guide book. It's the best, with written descriptions on each CCG, pictures of the cards, and of course checklists. For old CCGs, it is the definitive source of information, and I don't regret picking up my copy - nothing else compares as it transcends being just a price guide.

 * As for what is defined as a CCG, that is heavily sourced on the main collectible card game page. Lot's of different sources, and heavily drawing from the Scrye guide. But suffice it to say, a game must be collectible through booster packs or some other method, and you can't buy the entire game in a small number of purchases. The game must also have some element of strategy to it. With that in mind, Pez meets the criteria. Common deck games don't qualify as CCGs because they're often sold as a complete set, lack the collectible aspect, and the lack of personalizing your own deck may decrease the elements of strategy and collecting. Another factor with collectibility being key, is that there are definitely prototype games of the past that resemble CCGs in some aspect, but for them to be collectible, they had to actually be released in order to be collected, which rules out The Base Ball Card Game by Alleghany (though it fails in other ways too). Leitmotiv (talk) 20:28, 4 November 2019 (UTC)

Release dates
The introduction of the page states "Unless otherwise noted, all dates listed should be considered as the North American release date.". Hatalom Kártyái Kártyajáték and Kiválasztottak shows both of it's original Hungarian release, not the North American, I doubt any of them were released in NA to begin with. I've found an English site for HKK, but it was noted due to the massive amount of texts extensive translation is needed to become playable. I haven't found anything about an English version of M*K, and their webshop doesn't deliver outside Hungary at the moment, altough a week ago they noted they are planning EU distribution on their distributor's Facebook. That's why I added the "?" behind the release date, like some of the others have. 85.67.241.26 (talk) 07:39, 16 July 2020 (UTC)
 * The linked cited can be translated by Google. It mentions in late 1994 they came up with the idea and released it in 1995. So the date is not in question. Probably what is needed is a footnote after 1995 stating it was released in Hungary. Leitmotiv (talk) 18:21, 15 July 2020 (UTC)
 * I've added footnotes to both HKK and M*K. I also took the Liberty change the order of publishers of M*K 97-99 Valhalla, 2000-2003 CCG Art, 2004-2014 Két Mágus (AKA "Unoffical Era"), 2014- Két Mágus does the productions and development, Delta Vision is the publisher, M*K is official again. 85.67.241.26 (talk) 07:38, 16 July 2020 (UTC)
 * Excellent! Leitmotiv (talk) 16:44, 16 July 2020 (UTC)

Robotech publisher
The Robotech CCG's publisher links to the Lego theme of the same name, not the page for the actual company. Any idea on how to solve this? (sorry, I'm new here.) — Preceding unsigned comment added by 70.35.76.5 (talk) 18:52, 14 November 2020 (UTC)
 * Fixed! It appears there is no article for Hero Factory yet. Leitmotiv (talk) 18:57, 14 November 2020 (UTC)

Best Sellers
there needs to be a section dedicated to worldwide sales. Obviously, Magic or Pokemon are going to be #1, but it would still be helpful, since a google search only shows you ranks based on the site's opinion.2601:346:C201:60C0:B5F2:DF40:9BD3:BCF2 (talk) 23:26, 10 July 2021 (UTC)
 * That would be a whole new article. Wikipedia operates on cited sources, especially one composed of a list of sales. If you aren't finding anything on Google, chances are such an article is not possible at this time. I also believe most companies don't disclose sales/print runs. Either way, I think it would be a very short list: Magic, Pokemon, Yugioh, with a steep drop-off from there - a list is not very helpful. Leitmotiv (talk) 00:10, 11 July 2021 (UTC)

title: Talk:List of collectible card games


text:
Constructible strategy game

A constructible strategy game (CSG) (also spelled constructable strategy game) is a tabletop strategy game employing pieces assembled from components.

WizKids was the first to label a game as a CSG when they released their game Pirates of the Spanish Main in 2004. Internally, the term was coined by then-WizKids Communications Director Jason Mical to describe the game where players assemble ships from hulls, masts, and deck pieces punched out of credit card-like plastic (polystyrene). A second CSG from WizKids, Rocketmen, was released in summer 2005, and a NASCAR-themed CSG called Race Day came out later that year. Both Rocketmen and Race Day were later discontinued. WizKids now utilizes the term "PocketModel" to describe this genre, as with Star Wars PocketModel Trading Card Game and the modern Pirates of the Spanish Main website. White Wolf, Inc. released their own CSG, Racer Knights of Falconus, under their Arthaus Publishing imprint in mid-2005.

Wizards of the Coast was awarded in early 2007 for the constructible strategy game.

title: Constructible strategy game


text:
Word of the year

The word(s) of the year, sometimes capitalized as "Word(s) of the Year" and abbreviated "WOTY" (or "WotY"), refers to any of various assessments as to the most important word(s) or expression(s) in the public sphere during a specific year.

The German tradition, Wort des Jahres was started in 1971. The American Dialect Society's Word of the Year is the oldest English-language version, and the only one that is announced after the end of the calendar year, determined by a vote of independent linguists, and not tied to commercial interest. However, various other organizations also announce Words of the Year for a variety of purposes.

American Dialect Society
Since 1990, the American Dialect Society (ADS) has designated one or more words or terms to be the "Word of the Year" in the United States. In addition to the "Word of the Year", the society also selects words in other categories such as "Most Outrageous," "Most Creative," and "Most Likely to Succeed."

Australian National Dictionary Centre
The Australian National Dictionary Centre has announced a Word of the Year each since 2006. The word is chosen by the editorial staff, and is selected on the basis of having come to some prominence in the Australian social and cultural landscape during the year. The Word of the Year is often reported in the media as being Australia's word of the year, but the word is not always an Australian word.

Cambridge Dictionary
The Cambridge Dictionary Word of the Year, by Cambridge University Press & Assessment, has been published every year since 2015. The Cambridge Word of the Year is led by the data - what users look up - in the world's most popular dictionary for English language learners.

The 2023 Cambridge Dictionary Word of the Year is hallucinate, referencing AI hallucinations.

Collins English Dictionary
The Collins English Dictionary has announced a Word of the Year every year since 2013, and prior to this, announced a new 'word of the month' each month in 2012. Published in Glasgow, UK, Collins English Dictionary has been publishing English dictionaries since 1819.

Toward the end of each calendar year, Collins release a shortlist of notable words or those that have come to prominence in the previous 12 months. The shortlist typically comprises ten words, though in 2014 only four words were announced as the Word of the Year shortlist.

The Collins Words of the Year are selected by the Collins Dictionary team across Glasgow and London, consisting of lexicographers, editorial, marketing, and publicity staff, though previously the selection process has been open to the public.

Whilst the word is not required to be new to feature, the appearance of words in the list is often supported by usage statistics and cross-reference against Collins' extensive corpus to understand how language may have changed or developed in the previous year. The Collins Word of the Year is also not restricted to UK language usage, and words are often chosen that apply internationally as well, for example, fake news in 2017.

Dictionary.com
In 2010, Dictionary.com announced its first word of the year, 'change', and has done so in December every year since. The selection is based on search trends on the site throughout the year and the news events that drive them.

The following is the list of annual words since beginning with the first in 2010:

Macquarie Dictionary
The Macquarie Dictionary, which is the dictionary of Australian English, updates the online dictionary each year with new words, phrases, and definitions. These can be viewed on their website.

Each year the editors select a short-list of new words added to the dictionary and invite the public to vote on their favourite. The public vote is held in January and results in the People's Choice winner. The most influential word of the year is also selected by the Word of the Year Committee which is chaired by the Vice-Chancellor of the University of Sydney, Dr Michael Spence. The Editor of the Macquarie Dictionary, Susan Butler, is also a committee member. The Committee meets annually to select the overall winning words.

The following is the list of winning words since the Macquarie Word of the Year first began in 2006:

Merriam-Webster
The lists of Merriam-Webster's Words of the Year (for each year) are ten-word lists published annually by the American dictionary-publishing company Merriam-Webster, Inc., which feature the ten words of the year from the English language. These word lists started in 2003 and have been published at the end of each year. At first, Merriam-Webster determined its contents by analyzing page hits and popular searches on its website. Since 2006, the list has been determined by an online poll and by suggestions from visitors to the website.

The following is the list of words that became Merriam-Webster's Word of the Year since 2003:

Oxford
Oxford University Press, which publishes the Oxford English Dictionary and many other dictionaries, announces an Oxford Dictionaries UK Word of the Year and an Oxford Dictionaries US Word of the Year; sometimes these are the same word. The Word of the Year need not have been coined within the past twelve months but it does need to have become prominent or notable during that time. There is no guarantee that the Word of the Year will be included in any Oxford dictionary. The Oxford Dictionaries Words of the Year are selected by editorial staff from each of the Oxford dictionaries. The selection team is made up of lexicographers and consultants to the dictionary team, and editorial, marketing, and publicity staff.

Grant Barrett
Since 2004, lexicographer Grant Barrett has published an unranked words-of-the-year list, usually in The New York Times.

A Word a Year
Since 2004, Susie Dent, an English lexicographer has published a column, "A Word a Year", in which she chooses a single word from each of the last 101 years to represent preoccupations of the time. Susie Dent notes that the list is subjective. Each year, she gives a completely different set of words.

Since Susie Dent works for the Oxford University Press, her words of choice are often incorrectly referred to as "Oxford Dictionary's Word of the Year".

Other countries
Austria: Word of the year (Austria), since 1999

In Germany, a Wort des Jahres has been selected since 1972 (for year 1971) by the Society of the German Language. In addition, an Unwort des Jahres (Un-word of the year or No-no Word of the Year) has been nominated since 1991, for a word or phrase in public speech deemed insulting or socially inappropriate (such as "Überfremdung"). Similar selections are made each year since 1999 in Austria, 2002 in Liechtenstein, and 2003 in Switzerland. Since 2008, language publisher Langenscheidt supports a search for the German youth word of the year, which aims to find new words entering the language through the vernacular of young people.

In addition, several German dialects have their own Wort des Jahres selection: de:Plattdeutsches Wort des Jahres, de:Wort des Jahres (Sachsen), and de:Wort des Jahres (Südtirol)

In Denmark, the Word of the year (Denmark) has been selected by Mål og Mæle, a popular science language magazine, during 2006-1012 and since 2009 also by the Sproglaboratoriet radio program of the DR P1 radio channel in collaboration with Dansk Sprognævn (Danish Language Council).

Japan has held an annual word of the year contest called the "U-CAN New/Trendy Word Award" (Shingo ryūkōgo taishō) since 1984, sponsored by the Jiyu Kokuminsha publisher (by U-CAN since 2004). In addition, the Kanji of the Year (kotoshi no kanji) has been selected since 1995, and both the kanji and the word/phrase of the year often reflect current Japanese events and attitudes. For example, in 2011, following the Fukushima nuclear disaster, the frustratingly enigmatic phrase used by Japanese officials before the explosion regarding the possibility of a meltdown - "the possibility of recriticality is not zero" (Sairinkai no kanōsei zero de wa nai) - became the top phrase of the year. In the same year, the kanji for "bond" (i.e., family ties or friendship) became the kanji of the year, expressing the importance of collectiveness in the face of disaster.

Liechtenstein: Word of the year (Liechtenstein) since 2002

In Norway, the word of the year poll has been carried out since 2012.

In Portugal, the word of the year poll has been carried out since 2009.

In Russia, the word of the year poll has been carried out since 2007.

In Spain, a word of the year has been selected by Fundéu since 2013.

Switzerland: Word of the year (Switzerland), since 2003

In Ukraine, the word of the year poll has been carried out since 2013.

title: Word of the year


text:
100,000

100,000 (one hundred thousand) is the natural number following 99,999 and preceding 100,001. In scientific notation, it is written as 105.

Terms for 100,000
In Bangladesh, India, Pakistan and South Asia, one hundred thousand is called a lakh, and is written as 1,00,000. The Thai, Lao, Khmer and Vietnamese languages also have separate words for this number: แสน, ແສນ, សែន (all saen), and ức respectively. The Malagasy word is hetsy.

In the Netherlands, a 'ton' is a colloquialism for a denomination of 100.000 monetary units. In the guilders period a ton would denote 100.000 guilders. With the introduction of the euro, a ton would come to mean 100.000 euros. The usage is mostly limited to the financial sphere and the buying and selling of houses. It is not used in official settings because of the ambiguity with commonly used metric tonne. While usage is common in the Netherlands, it sees almost no use in Belgium.

In Cyrillic numerals, it is known as the legion : or.

Values of 100,000
In astronomy, 100,000 metres, 100 kilometres, or 100 km (62 miles) is the altitude at which the Fédération Aéronautique Internationale (FAI) defines spaceflight to begin.

In paleoclimatology, the 100,000-year problem is a mismatch between the temperature record and the modeled incoming solar radiation.

In the Irish language, céad míle fáilte is a popular greeting meaning "a hundred thousand welcomes".

100,001 to 199,999

 * 100,003 = smallest 6-digit prime number
 * 100,128 = smallest triangular number with 6 digits and the 447th triangular number
 * 100,151 = twin prime with 100,153
 * 100,153 = twin prime with 100,151
 * 100,255 = Friedman number
 * 100,489 = 3172, the smallest 6-digit square
 * 101,101 = smallest palindromic Carmichael number
 * 101,723 = smallest prime number whose square is a pandigital number containing each digit from 0 to 9
 * 102,564 = The smallest parasitic number
 * 103,049 = Schröder–Hipparchus number
 * 103,680 = highly totient number
 * 103,769 = the number of combinatorial types of 5-dimensional parallelohedra
 * 103,823 = 473, the smallest 6-digit cube and nice Friedman number (−1 + 0 + 3×8×2)3
 * 104,480 = number of non-isomorphic set-systems of weight 14.
 * 104,723 = the 9,999th prime number
 * 104,729 = the 10,000th prime number
 * 104,869 = the smallest prime number containing every non-prime digit
 * 104,976 = 184, 3-smooth number
 * 105,071 = number of triangle-free graphs on 11 vertices
 * 105,558 = number of partitions of 46
 * 105,664 = harmonic divisor number
 * 108,968 = number of signed trees with 11 nodes
 * 109,376 = automorphic number
 * 110,880 = highly composite number
 * 111,111 = repunit
 * 111,777 = smallest natural number requiring 17 syllables in American English, 19 in British English
 * 113,634 = Motzkin number for n = 14
 * 114,243/80,782 ≈ √2
 * 114,689 = prime factor of F12
 * 115,975 = Bell number
 * 116,281 = 3412, square number, centered decagonal number, 18-gonal number
 * 117,067 = first vampire prime
 * 117,649 = 76
 * 117,800 = harmonic divisor number
 * 120,032 = number of primitive polynomials of degree 22 over GF(2)
 * 120,284 = Keith number
 * 120,960 = highly totient number
 * 121,393 = Fibonacci number
 * 123,717 = smallest digitally balanced number in base 7
 * 123,867 = number of trees with 18 unlabeled nodes
 * 124,754 = number of partitions of 47
 * 125,673 = logarithmic number
 * 127,777 = smallest natural number requiring 18 syllables in American English, 20 in British English
 * 127,912 = Wedderburn–Etherington number
 * 128,981 = Starts the first prime gap sequence of 2, 4, 6, 8, 10, 12, 14
 * 129,106 = Keith number
 * 130,321 = 194
 * 131,071 = Mersenne prime
 * 131,072 = 217 and largest determinant of a (real) {0,1}-matrix of order 15.
 * 131,361 = Leyland number
 * 134,340 = Pluto's minor planet designation
 * 135,135 = double factorial of 13
 * 135,137 = Markov number
 * 142,129 = 3772, square number, dodecagonal number
 * 142,857 = Kaprekar number, smallest cyclic number in decimal.
 * 144,000 = number with religious significance
 * 147,273 = number of partitions of 48

 * 147,640 = Keith number
 * 148,149 = Kaprekar number
 * 152,381 = unique prime in base 20
 * 156,146 = Keith number
 * 155,921 = smallest prime number being the only prime in an interval from 100n to 100n + 99
 * 160,000 = 204
 * 160,176 = number of reduced trees with 26 nodes
 * 161,051 = 115
 * 161,280 = highly totient number
 * 166,320 = highly composite number
 * 167,400 = harmonic divisor number
 * 167,894 = number of ways to partition {1,2,3,4,5,6,7,8} and then partition each cell (block) into subcells.
 * 173,525 = number of partitions of 49
 * 173,600 = harmonic divisor number
 * 174,680 = Keith number
 * 174,763 = Wagstaff prime
 * 176,906 = number of 24-bead necklaces (turning over is allowed) where complements are equivalent
 * 177,147 = 311
 * 177,777 = smallest natural number requiring 19 syllables in American English, 21 in British English
 * 178,478 = Leyland number
 * 181,440 = highly totient number
 * 181,819 = Kaprekar number
 * 182,362 = number of 23-bead binary necklaces with beads of 2 colors where the colors may be swapped but turning over is not allowed
 * 183,186 = Keith number
 * 183,231 = number of partially ordered set with 9 unlabeled elements
 * 187,110 = Kaprekar number
 * 189,819 = number of letters in the longest English word, taking 3 hours to pronounce
 * 194,481 = 214
 * 195,025 = Pell number, Markov number
 * 196,418 = Fibonacci number, Markov number
 * 196,560 = the kissing number in 24 dimensions
 * 196,883 = the dimension of the smallest nontrivial irreducible representation of the Monster group
 * 196,884 = the coefficient of q in the Fourier series expansion of the j-invariant. The adjacency of 196883 and 196884 was important in suggesting monstrous moonshine.
 * 199,999 = prime number.

200,000 to 299,999

 * 202,717 = k such that the sum of the squares of the first k primes is divisible by k.
 * 206,098 – Large Schröder number
 * 206,265 = rounded number of arc seconds in a radian (see also parsec), since $180 × 60 × 60⁄\pi$ = 206,264.806...
 * 207,360 = highly totient number
 * 208,012 = the Catalan number C12
 * 208,335 = the largest number to be both triangular and square pyramidal
 * 208,495 = Kaprekar number
 * 212,159 = smallest unprimeable number ending in 1, 3, 7 or 9
 * 221,760 = highly composite number
 * 222,222 = repdigit
 * 224,737 = the 20,000th prime number
 * 227,475 = Riordan number
 * 234,256 = 224
 * 237,510 = harmonic divisor number
 * 238,591 = number of free 13-ominoes
 * 241,920 = highly totient number
 * 242,060 = harmonic divisor number
 * 248,832 = 125, 100,00012, AKA a gross-great-gross (10012 great-grosses); the smallest fifth power that can be represented as the sum of only 6 fifth powers: 125 = 45 + 55 + 65 + 75 + 95 + 115
 * 255,168 = number of ways to play tic tac toe
 * 262,144 = 218; exponential factorial of 4; a superperfect number
 * 262,468 = Leyland number
 * 268,705 = Leyland number
 * 274,177 = prime factor of the Fermat number F6
 * 275,807/195,025 ≈ √2
 * 276,480 = number of primitive polynomials of degree 24 over GF(2)
 * 277,200 = highly composite number
 * 279,841 = 234
 * 279,936 = 67
 * 280,859 = a prime number whose square 78881777881 is tridigital
 * 291,400 = number of non-equivalent ways of expressing 100,000,000 as the sum of two prime numbers
 * 293,547 = Wedderburn–Etherington number
 * 294,001 = smallest weakly prime number in base 10
 * 294,685 = Markov number
 * 298,320 = Keith number

300,000 to 399,999

 * 310,572 = Motzkin number
 * 314,159 = pi-prime
 * 316,749 = number of reduced trees with 27 nodes
 * 317,811 = Fibonacci number
 * 317,955 = number of trees with 19 unlabeled nodes
 * 318,682 = Kaprekar number
 * 325,878 = Fine number
 * 326,981 = alternating factorial
 * 329,967 = Kaprekar number
 * 331,776 = 244
 * 332,640 = highly composite number; harmonic divisor number
 * 333,333 = repdigit
 * 333,667 = sexy prime and unique prime
 * 333,673 = sexy prime with 333,679
 * 333,679 = sexy prime with 333,673
 * 337,500 = 22 × 33 × 55
 * 337,594 = number of 25-bead necklaces (turning over is allowed) where complements are equivalent
 * 349,716 = number of 24-bead binary necklaces with beads of 2 colors where the colors may be swapped but turning over is not allowed
 * 351,351 = only known odd abundant number that is not the sum of some of its proper, nontrivial (i.e. >1) divisors.
 * 351,352 = Kaprekar number
 * 355,419 = Keith number
 * 356,643 = Kaprekar number
 * 356,960 = number of primitive polynomials of degree 23 over GF(2)
 * 360,360 = harmonic divisor number; smallest number divisible by the numbers from 1 to 15 (there is no smaller number divisible by the numbers from 1 to 14 since any number divisible by 3 and 5 must be divisible by 15)
 * 362,880 = 9!, highly totient number
 * 369,119 = prime number which divides the sum of all primes less than or equal to it
 * 369,293 = smallest prime with the property that inserting a digit anywhere in the number will always yield a composite
 * 370,261 = first prime followed by a prime gap of over 100
 * 371,293 = 135, palindromic in base 12 (15AA5112)
 * 389,305 = self-descriptive number in base 7
 * 390,313 = Kaprekar number
 * 390,625 = 58
 * 397,585 = Leyland number

400,000 to 499,999

 * 409,113 = sum of the first nine factorials
 * 422,481 = smallest number whose fourth power is the sum of three smaller fourth powers
 * 423,393 = Leyland number
 * 426,389 = Markov number
 * 426,569 = cyclic number in base 12
 * 437,760 to 440,319 = any of these numbers will cause the Apple II+ and Apple IIe computers to crash to a monitor prompt when entered at the BASIC prompt, due to a short-cut in the Applesoft code programming of the overflow test when evaluating 16-bit numbers. Entering 440000 at the prompt has been used to hack games that are protected against entering commands at the prompt after the game is loaded.
 * 444,444 = repdigit
 * 456,976 = 264
 * 461,539 = Kaprekar number
 * 466,830 = Kaprekar number
 * 470,832 = Pell number
 * 483,840 = highly totient number
 * 492,638 = number of signed trees with 12 nodes
 * 498,960 = highly composite number
 * 499,393 = Markov number
 * 499,500 = Kaprekar number

500,000 to 599,999

 * 500,500 = Kaprekar number, sum of first 1,000 integers
 * 509,203 = Riesel number
 * 510,510 = the product of the first seven prime numbers, thus the seventh primorial. It is also the product of four consecutive Fibonacci numbers—13, 21, 34, 55, the largest such sequence of any length to be also a primorial. And it is a double triangular number, the sum of all even numbers from 0 to 1428.
 * 514,229 = Fibonacci prime,
 * 518,859 = Schröder–Hipparchus number
 * 524,287 = Mersenne prime
 * 524,288 = 219
 * 524,649 = Leyland number
 * 525,600 = minutes in a non-leap year
 * 527,040 = minutes in a leap year
 * 531,441 = 312
 * 533,169 = Leyland number
 * 533,170 = Kaprekar number
 * 537,824 = 145
 * 539,400 = harmonic divisor number
 * 548,834 = equal to the sum of the sixth powers of its digits
 * 554,400 = highly composite number
 * 555,555 = repdigit
 * 586,081 = number of prime numbers having seven digits.
 * 593,661 = the ID of the most commonly used custom song in Geometry Dash (Xtrullor - Supernova)
 * 599,999 = prime number.

600,000 to 699,999

 * 604,800 = number of seconds in a week
 * 614,656 = 284
 * 625,992 = Riordan number
 * 629,933 = number of reduced trees with 28 nodes
 * 645,120 = double factorial of 14
 * 646,018 = Markov number
 * 649,532 = number of 26-bead necklaces (turning over is allowed) where complements are equivalent
 * 664,579 = the number of primes under 10,000,000
 * 665,280 = highly composite number
 * 665,857/470,832 ≈ √2
 * 666,666 = repdigit
 * 671,092 = number of 25-bead binary necklaces with beads of 2 colors where the colors may be swapped but turning over is not allowed
 * 676,157 = Wedderburn–Etherington number
 * 678,570 = Bell number
 * 694,280 = Keith number
 * 695,520 = harmonic divisor number

700,000 to 799,999

 * 700,001 = prime number.
 * 707,281 = 294
 * 720,720 = superior highly composite number; colossally abundant number; smallest number divisible by the numbers from 1 to 16
 * 725,760 = highly totient number
 * 726,180 = harmonic divisor number
 * 729,000 = 903
 * 739,397 = largest prime that is both right- and left-truncatable.
 * 742,900 = Catalan number
 * 753,480 = harmonic divisor number
 * 759,375 = 155
 * 765,623 = emirp, Friedman prime 56 × 72 − 6 ÷ 3
 * 777,777 = repdigit, smallest natural number requiring 20 syllables in American English, 22 in British English, largest number in English not containing the letter 'i' in its name
 * 783,700 = initial number of third century xx00 to xx99 (after 400 and 1,400) containing seventeen prime numbers {783,701, 783,703, 783,707, 783,719, 783,721, 783,733, 783,737, 783,743, 783,749, 783,763, 783,767, 783,779, 783,781, 783,787, 783,791, 783,793, 783,799}
 * 799,999 = prime number.

800,000 to 899,999

 * 810,000 = 304
 * 823,065 = number of trees with 20 unlabeled nodes
 * 823,543 = 77
 * 825,265 = smallest Carmichael number with 5 prime factors
 * 832,040 = Fibonacci number
 * 853,467 = Motzkin number
 * 857,375 = 953
 * 873,612 = 11 + 22 + 33 + 44 + 55 + 66 + 77
 * 888,888 = repdigit
 * 890,625 = automorphic number

900,000 to 999,999

 * 900,001 = prime number
 * 901,971 = number of free 14-ominoes
 * 909,091 = unique prime in base 10
 * 923,521 = 314
 * 925,765 = Markov number
 * 925,993 = Keith number
 * 950,976 = harmonic divisor number
 * 956,619: 956619^2=915119911161, and only the digits 1, 5, 6 and 9 are used in both this number and its square.
 * 967,680 = highly totient number
 * 970,299 = 993, the largest 6-digit cube
 * 998,001 = 9992, the largest 6-digit square. The reciprocal of this number, in its expanded form, lists all three-digit numbers in order except 998.
 * 998,991 = largest triangular number with 6 digits and the 1413th triangular number
 * 999,983 = largest 6-digit prime number
 * 999,999 = repdigit. Rational numbers with denominators 7 and 13 have 6-digit repetends when expressed in decimal form, because 999999 is the smallest number one less than a power of 10 that is divisible by 7 and by 13, and it is the largest number in English not containing the letter 'l' in its name.

Prime numbers
There are 9,592 primes less than 105, where 99,991 is the largest prime number smaller than 100,000.

Increments of 105 from 100,000 through a one million have the following prime counts:

In total, there are 68,906 prime numbers between 100,000 and 1,000,000.
 * 8,392 primes between 100,000 and 200,000. This is a difference of 1,200 primes from the previous range.
 * 104,729 is the 10,000th prime in this range.
 * 199,999 is prime.
 * 8,013 primes between 200,000 and 300,000. A difference of 379 primes from the previous range.
 * 224,737 is the 20,000th prime.
 * 7,863 primes between 300,000 and 400,000. A difference of 150 primes from the previous range.
 * 350,377 is the 30,000th prime.
 * 7,678 primes between 400,000 and 500,000. A difference of 185 primes from the previous range. Here, the difference increases by a count of 35.
 * 479,909 is the 40,000th prime.
 * 7,560 primes between 500,000 and 600,000. A difference of 118 primes from the previous range.
 * 7,560 is the twentieth highly composite number.
 * 599,999 is prime.
 * 7,445 primes between 600,000 and 700,000. A difference of 115 primes from the previous range.
 * 611,953 is the 50,000th prime.
 * 7,408 primes between 700,000 and 800,000. A difference of 37 primes from the previous range.
 * 700,001 and 799,999 are both prime.
 * 746,773 is the 60,000th prime.
 * 7,323 primes between 800,000 and 900,000. A difference of 85 primes from the previous range. Here, the difference increases by a count of 48.
 * 882,377 is the 70,000th prime.
 * 7,224 primes between 900,000 and 1,000,000. A difference of 99 primes from the previous range. The difference increases again, by a count of 14.
 * 900,001 is prime.

title: 100,000


text: User talk:203.51.32.151

title: User talk:203.51.32.151