Chang-Sheng Wang

Pierre H Dixneuf

Jean-François Soulé
email: jean-francois.soule@univ-rennes1.fr

Metal-free C(sp(3))-H bond sulfonyloxylation of 2-alkylpyridines and alkylnitrones

Pyridin-2-ylmethyl tosylate derivatives are obtained in high yields from 2-alkylpyridine 1-oxides via a [3,3]-sigmatropic rearrangement of the adduct between 2-alkylpridine 1-oxides with benzenesylfonyl chlorides. Moreover, alkylnitrones also undergo [3,3]-sigmatropic rearrangement to give α-tosylated ketones after hydrolysis. Substitution reactions with nucleophiles then lead to diverse useful functionalizations for the synthesis of pincer ligands.

Alkyl sulfonates, such as alkyl tosylates, are typical substrates for SN 2 reactions. Compared to alkyl halides, they often display higher thermal/light stability and resistance to radicaltriggered side reactions. They are generally synthetized from alcohols by condensation reactions with benzenesulfonyl chlorides.

A more straightforward access to these synthetically useful synthons would involve the direct transformation of inert C(sp 3 )-H bond into C-OSO 2 R bond. 1 In 2015, Dong and co-workers reported an elegant approach for the synthesis of β-sulfonyloxylated alcohols through a palladium-catalyzed regioselective C(sp 3

)-H bond functionalizations of masked alcohols bearing 8formylquinoline-derived oxime as directing group (Figure 1a).

2

The reaction has employed p-toluenesulfonic acid as sulfonyloxation agent and N-fluorobenzenesulfonimide (NFSI) as the oxidant. Pyridin-2-ylmethyl tosylate derivatives, which are important building blocks for the preparation of metal pincer complexes, 3 are generally prepared from pyridin-2ylmethanol derivatives. In 2017, our group has succeeded the C(sp 3 )-H bond benzoxylation of 2-alkylpyridine derivatives through copper-catalyzed oxidative esterification of 2alkylpyridine 1-oxides with aldehydes followed by [3,3]sigmatropic rearrangement (Figure 1b). 4 The same year, Chen, Fu and co-workers reported metal-free conditions for the phosphorylation of 2-alkylpyridine and nitrone derivatives via a similar [3,3]-sigmatropic rearrangement (Figure 1c). To the best of our knowledge, there is no example of [3,3]sigmatropic rearrangement of 2-alkylpyridine 1-oxides with benzenesulfonyl chlorides, although it could provide an efficient synthetic method to pyridin-2-ylmethyl tosylate derivatives.

We decided to tackle this challenge by investigating the reactivity of 2-alkylpyridine 1-oxides in the presence of benzenesulfonyl chlorides (Figure 1d). )-H Bond Sulfonyloxylation and Functionation of 2-Alkyl Pyridines via [3,3]-Sigmatropic Rearrangements

We selected 2,6-dimethylpyridine 1-oxide and tosyl chloride as model substrates to study the formal C(sp 3 )-H bond sulfonyloxylation through a [3,3]-rearrangement. Surprisingly, the expected product 1 was not formed in the presence of potassium carbamate (K 2 CO 3 ) as base in acetonitrile (CH 3 CN), although those reaction conditions have been employed by the Sledeski' group for the C(sp 3)-H bond sulfonyloxylation of 2-methylquinoline 1-oxide (Table 1, entry 1).

6

No reaction occurred in CH 2 Cl 2 when K 2 CO 3 and KOH were employed as base, whereas in the presence of 2 equivalents of organic base such as triethylamine (Et 3 N), the sulfonyloxylated product 1 was obtained in 12% yield (Table 1, entries 2-4). Then, we investigated the influence of nature of other solvents. The reaction is not operative in CH 3 CN, dichloroethane (DCE) and ethanol (Table 1, entries 4-7). However, in THF the desired product 1 was obtained in a high yield of 72% (Table 1, entry 8). The use of 1.5 equivalents of tosyl chloride allowed to improve the yield of the sulfonyloxylated product 1 to 82% yield and even better (87%) using 2.5 equivalents of base (Table 1, entries 9 and10). [a] Determined by GC-MS analysis using n-dodecane as internal standard, isolated yield is shown in parentheses

With the best conditions in hands, namely 2.5 equivalents of Et 3 N as base in THF at room temperature, we turn our attention to the scope of the reaction. First, we examined the reactivity of other substituted benzenesulfonyl chlorides with 2,6-dimethylpyridine 1-oxide (Scheme 1). Benzenesulfonyl chloride displays a low reactivity, as the (6-methylpyridin-2yl)methyl benzenesulfonate 2 is isolated in only 23% yield. When benzenesulfonyl chloride is substituted by an electrondonating group such as tBu or OMe at the para-position, the sulfonyloxylated products 3 and 4 are obtained in 62% and 78% yield, respectively. However, when the benzenesulfonyl chloride bears an electron-poor substituent at the para position such as NO 2 CN or CF3, the desired product has not been isolated due to its instability. Benzenesulfonyl chlorides bearing an electron-withdrawing group at meta position such F displayed good reactivity, allowing the formation of desired product 5 in 53% yield. The reaction is not sensitive to the steric hindrance, as from 2,4,6-triisopropylbenzenesulfonyl chloride, the sulfonyloxylated products 6 is isolated in an excellent yield. Heteroarylsulfonly chloride such as methyl 3-(chlorosulfonyl)thiophene-2-carboxylate can be also employed under this reaction conditions with 2,6-dimethylpyridine 1oxide to prepare the sulfonyl bridged bis-heterocycle 7 in 54% yield. Similar bridged structures exhibit important biological activities and are pharmaceutical drug precursors. )-H tosyloxylated product. 8 This reaction is successful for the formation of tertiary carbons, as from 2-ethylpyridine 1-oxide the tosyloxylated product 9 is obtained in 55% yield.

The reaction tolerated a bromo or an ester substituent on the 2-methylpyridine 1-oxide partner allowing the formation of 10 and 11 in good yield, respectively. We also succeeded in the desymmetrization of one methyl group of 2,4,6-collidine 1oxide with the formation of mono-tosyloxylated product 12 in 69% yield. Finally, 2-methylquinoline 1-oxide nicely reacted under these reaction conditions to deliver 13 in good yield. Next, we investigated the reactivity of nitrones, derived from the in-situ condensation of acetophenones with 1methylhydroxylamine hydrochloride, in the presence of tosyl chloride (Scheme 3). We are pleased to find that using only 1 equivalent of Et 3 N, the nitrone reacts with tosyl chloride followed by [3,3] sigmatropic rearrangement and then by in situ hydrolysis to yield α-keto tosylate 14 in 76% yield. The use of 2 equivalent of base lead to lower yield in 14 due to the formation of degradation products. Interestingly, this reaction sequence for the α-tosyloxylation of enolizable ketones tolerates halo substituents (e.g., X = F, Br, I) on the aryl group of the acetophenone derivatives allowing the formation of the tosylates 16-18 in high yields. Noteworthy, only a limited number of synthetic methods toward α-keto tosylates have been reported. 9

Most of them employed a two-step procedure or required the use of stoichiometric amount of a strong oxidant. In contrast, our method based on [3,3]rearrangement of nitrone-tosylate adducts has some advantages, as it takes place under mild reaction conditions, with user-friendly procedure and the reactants are available at an affordable cost. Then, the intermediate C spontaneous undergoes [3,3]-rearrangement leading to the formation of sulfonyloxylated pyridine D. The driving force of this [3,3]rearrangement is the rearomatization of the pyridine unit. We proposed a similar pathway with nitrone (Figure 2b). The addition-elimination of 2-methyl nitrone E to arylsulfonyl chloride affords F, which undergoes deprotonation of its acidic C( sp3 )-H bond followed [3,3]-rearrangement to afford the imine H. In the presence of water the imine H is hydrolyzed to the sulfonyloxylated ketone I.

Conclusions

In summary, the present study provides a convenient and efficient approach for the diverse functionalization of alkyl pyridines and aryl alkyl ketones through the direct replacement of an C(sp 3)-H bond with a good leaving group (OTs). The formation of sulfonyloxylated pyridines is based on [3,3] rearrangement of sulfonated pyridinium intermediate, whereas the α-keto sulfonated are also obtained by a [3,3] rearrangement of sulfonated nitrone intermediate. Both rearrangements operate under very mild conditions in the presence of only triethylamine and did not required the use of oxidant.

5

 5

  NC_Journées des Chargés de Recherche -Promotion 2013 NC_Journées des Chargés de Recherche -Promotion 2013

Figure 1 .

 1 Figure 1. Previous C(sp 3

7 Scheme 1 .

 71 Scheme 1. Scope of Benzenesulfonly Chloride in C(sp 3 )-H Bond Sulfonyloxylation of 2,6-Dimethylpyridine 1-Oxide

Scheme 2 .

 2 Scheme 2. Scope of 2-Alkylpyridine 1-Oxides in Tosyloxylation with Tosyl Chlorides

Scheme 3 .

 3 Scheme 3.[3,3] Rearrangement Reaction of Nitrone with Tosyl or Benzenesulfonyl Chlorides

Figure 2 .

 2 Figure 2. Proposed Mechanistic Pathways: a) for the Sulfonyloxylation of 2-Alkylpyridine 1-Oxides; b) for the Sulfonyloxylation of Nitrone Derivatives

Scheme 4 .

 4 Scheme 4. Diversification of Tosyloxylated Pyridine 1 via Leaving Group Strategy

Table 1 .

 1 Optimization of the Reaction Conditions

	Entry x / y	Base (z equiv.)	Solvent	Yield in 1 (%)
	1	1:1.1	K2CO3 (2)	CH3CN	0
	2	1:1.1	K2CO3 (2)	CH2Cl2	0
	3	1:1.1	KOH (2)	CH2Cl2	0
	4	1:1.1	Et3N (2)	CH2Cl2	12
	5	1:1.1	Et3N (2)	CH3CN	0
	6	1:1.1	Et3N (2)	DCE	0
	7	1:1.1	Et3N (2)	EtOH	0
	8	1:1.1	Et3N (2)	THF	72
	9	1:1.5	Et3N (2)	THF	82
	10	1:1.5	Et3N (2.5)	THF	87 (81)

)-H bond of 2alkylpyridines and nitrone into C-OSO 2 R bond has been described.

Acknowledgements

C.-S.W. acknowledges the China Scholarship Council (CSC) fora PhD grant.

Conflicts of interest

"There are no conflicts to declare".

Notes and references


"THE WORK OF GLOBALIZATION": HOW STANDARDIZATION MAY IMPACT THE GLOBALIZATION OF WORK

Are globalization and market mechanism one of the same thing? Does the globalization of product markets entail a glo balization of labor? Does the current move towards globalization favor the countries with a low-cost working force and does it jeopardize the countries where workers benefit from better legal protection and incomes? In order to answer this type of questions, I'll try to highlight the link between the impossible glo balization of work and the continuous emergence of standardization as a "work of globalization". In order to seize the issues at stake, we could for instance listen to a gathering of socially aware organizations-the "group for ethics on l abels" (collectif de l'éthique sur l'étiquette)-which militates in order to... make the consumers aware of the often scandalous working conditions in which the products they buy are made. […] This public awareness campaign is aimed at encouraging consumers to buy products of good social quality, products made in decent conditions. For the moment, consumers do not have any reliable information on this subject. That's why the group for ethics on labels proposes to put pressure on distributors in order to make them accept to participate in the building of an information system (social label). […] To create the social label, the group tries to rely on the international system of standardization and certification, in which governmental agencies are deeply involved: ISO (International Standards Organization), CEN (European Committee for Standardization) and AFNOR (French Standards Organization). 1With the initiative of the group for ethics on label, we discover a new issue for a globalized labor market: that of the international standardization of labor. In the above statement, one clearly has to rely on the historical know-how of industrial standardization ("ISO", "CEN", "AFNOR") in order to set up a standard and a certificate ("social label") liable to lead to the codification and traceability of labor ("reliable information") and relate the evaluation of products to the quality of their production ("social quality"). In order to measure the impact of this initiative on labor and globalization, it is first necessary to replace it among three other alternative solutions. These solutions were proposed by international regulative agencies (World Trade Organization and International Labor Organization), by multinational companies (codes of conduct) and by the Council on Economic Priorities (SA 8000 standard).

I. WTO versus ILO, or the impossible common regulation of commodities and labor

The place of labor in international trade is of the greatest interest for the two worldwide organizations that deal with such issues: WTO for trade, ILO for labor. If, on the one hand, the ILO preamble asserts that "the non-adoption by any nation of a really human labor regulation is an obstacle for the efforts of the other nations which are eager to improve the situation of workers in their own countries", on the other hand the WTO (as the protector of free trade) carries the implicit idea that social progress is not the condition but the consequence of an enlarged trade (Siroën, 1998). The separation of these two instances makes it very difficult to improve the way in which labor problems are taken into account in world trade regulation. Of course, the OECD tried to gather the two points of view: "We reaffirm our commitment to respect fundamental labor standards that are internationally recognized. The International Labor Organization (ILO) is the authority liable to set up these standards and deal with them, and we declare that we support the activities it conducts in order to promote such standards. We think that economic growth and development favored by an increase of commercial exchanges and by a further liberalization of trade contribute to the promotion of these standards. We reject the use of labor standards for protectionist purposes, and we admit that the comparative advantage of developing countries with low wages should absolutely not be called into question. In this respect, we note that the WTO and ILO secretarial offices will continue to collaborate at they currently do" (Declaration of the ministry conference of OECD countries, December 1996, Singapore, quoted in Siroën 1998, p. 59, n. 81).

But we see that the institutional separation of the two questions-labor and human beings' protection on the ILO side [START_REF] Bonvin | L'organisation internationale du travail. Étude sur une agence productrice de normes[END_REF], trade and objects' circulation on the WTO side (Siroën, 1998)-hinders any real progress. In the quoted declaration, the middle of the argument literally "destroys" the intentions expressed at its beginning and its end. Without a joint treatment of trade and labor matters, the one will continue to tolerate low wages in order to avoid any kind of "social protectionism" ( cf. supra), while the others will persist in condemning the same practices in order to fight against "social dumping" (cf. the old idea of a "social clause" for international trade contracts that ILO has always supported [START_REF] Servais | La clause sociale dans les traités de commerce: prétention irréaliste ou instrument du progrès social ?[END_REF][START_REF] Siroën | Existe-t-il une justification économique à la clause sociale? Quelques éléments de réflexion[END_REF][START_REF] Grenouillet | Fair trade and free trade: état des lieux[END_REF]).

II. The ambiguities of voluntary codes of socially responsible behavior

What international organizations cannot do because of their separation, multinational companies try to do for the fulfillment of their own interest... under public pressures. Violent criticisms were recently launched against the exploitation of labor in developing countries in the frame of international subcontracting. For instance, the sport shoe manufacturer Nike was the butt of public denunciations and boycott calls in the American media 2 , for the incredibly low wages and the physical and sexual abuses that are supposed to occur in the Vietnamese and Chinese plants working for the company 3 . In order to answer these critics, Nike decided to adopt a voluntary code of conduct. This type of code proclaims the "responsibility [of businesses] for the protection of workers who manufacture their products". The company adopting such a code generally commits itself to proscribe hard work, child labor, discrimination, and to provide satisfactory working conditions of health and safety, to limit the weekly working time to 60 hours, to guarantee union rights, etc. 4 . The problem is of course that these codes are more "displayed" than "enforced" 5 , since their implementation and control rely on the single responsibility of the concerned companies. This difficulty is the argument raised by Nike's competitor Reebok, in order to justify its own refusal to implement the same form of "social responsibility". Indeed, according to Reebok, the only way to give legitimacy to voluntary codes would be to set up an independent auditing system. In doing so, Reebok implicitly recognizes the emergence of "ethics" as a new way to compete at the global level (cf. infra). From this point onward, the old debate that still preoccupies WTO and ILO-free trade versus social protection-is progressively replaced by a new choice: the choice of the best way to compete through labor protection.

III. Social standardization: an intermediary solution

On the one hand, the will to solve the problems at the global level while maintaining the institutional separation between the social side (for ILO) and the economic side (for WTO) of negotiations leads to paralysis. On the other hand, the opportunistic adoption of voluntary codes of conduct leads to hypocrisy. But a new way to overcome these two deadlocks is now emerging: it is the development of a form of "social standardization". Social standardization would set up standards for working conditions and give a "social label" to the companies that would implement it; of course the attribution of the label would be guaranteed through a third party auditing system 6 . As we guessed it, this third way is followed in France by the group for ethics on labels, and more generally it is the way which is being promoted internationally by all those who advocate the development of a standardization and certification of labor.

The most advanced endeavor in this field is the setting of the "SA 8000" standard. This standard is directly inspired by the quality management standards, and is thus oriented towards the third party certification of the firms following the standard specifications. The SA 8000 device was officially presented on October 15, 1997. This device was developed under the authority of the Council on Economic Priorities, a nonprofit organization working since 1969 for the betterment of the social and environmental behavior of companies. The Council gave the responsibility for the standard development to an had hoc agency: the CEPAA (Council on Economic Priorities Accreditation Agency). This agency gathers nonprofit organization (such as the National Child Labor Committee), trade unions, companies (like Reebok), and scholars, following a template that greatly recalls the functioning of official standardization agencies 7 .

The SA 8000 standard mixes the general principles of ILO 8 with quality management tools (e.g. the ISO 9000 series) 9 . Indeed, the standard is founded on eight fundamental principles: the banning of child labor and hard labor, the implementation of safety and health policies, the guarantee of union rights and collective bargaining, the banning of any kind of discrimination, the banning of any physical or moral violence, the limitation of the working time to 48 hours and of the overtime work to 12 hours weekly, the fixing of wages at a level which is at least equal to the minimum legal rate and which can at least cover the employees' basic needs. But whereas the ILO was only able to formulate a list of points which could hardly be implemented and verified, because they 7. http:// www.cepaa.org 8. More precisely, the standard refers not only to ILO conventions, but also to the Universal Bill of Human Rights and to the United Nations Conve ntion on Children Rights. 9. For an analysis of the social impact of the ISO 9000 standards, see [START_REF] Cochoy | L'âne de Buridan revisité: l'homme économique moderne entre marketing et normalisation des produits[END_REF] ultimately depended on the goodwill of nations [START_REF] Swinnerton | Labor Standards in the Context of a Global Economy[END_REF], the SA 8000 standard tries to concentrate its effort at the local a nd managerial level of productive organizations. The effort is twofold. On the one hand, the standard asks for the setting of orga nizational devices liable to "manage" its implementation: it requires that a management representative took the responsibility of managing the standard; it calls for the setting of a traceability of the social practices of the company, etc.. On the other hand and most importantly, the standard includes the principle of third party audits endorsed by specialized consulting agencies: since the inception of the SA 8000 standard, some of the most prominent consulting groups have joined the system (Société Générale de Surveillance, Bureau Veritas, Intertek Testing Service…). The result of such a combination of legal principles and managerial techniques is very ambiguous. On the one hand, the SA 8000 standard is somewhat dishonest, since it asks no more than international law requirements while presenting it as a privilege and a competitive advantage10 . On the other hand, the SA 8000 standard may promote the legal standards more efficiently than the law itself, by connecting legal issues with market and managerial forces.

Conclusion

What can we think about social standardization? What is its potential impact on the global job market? This device being still at its experimental stage, a direct answer to such questions would be premature. Nevertheless, if the SA 8000 standard is replaced in the frame of the general transformations that preceded or accompanied it, it seems that some evolutions may be foreshadowed. We can notice that the SA 8000 device clearly takes the standardization of quality as its model and stepping stone: its first objective is to open a company certification, before developing a "social label" as a potential commercial weapon. Given this initiative of the supply side, it is important to know that, on the demand side, consumers have learned for a long time how to go beyond the appearances of products, in order to focus on brand, warranties [START_REF] Cochoy | L'âne de Buridan revisité: l'homme économique moderne entre marketing et normalisation des produits[END_REF], technical characteristics (Cochoy, 2000) and more recently manufacturing conditions (Cochoy, 2001) and the environmental dimension of products [START_REF] Menon | Enviropreneurial Marketing Strategy: The Emergence of Corporate Environmentalism as Market Strategy[END_REF] 11 . Given this general evolution, it is highly probable that the idea of "social certification" might become, just like product traceability or environment care, a component of goods and services that may be demanded by consumers. In any case, this is evidenced by the convergent results of several surveys dealing with consumer's receptiveness to "ethical" consumption 12 , and by the works of "political consumerism" specialists 13 .

In other words, the emergence of a consumer preference for the social characteristics of products is in fact just a particular case of a more general drive towards the incorporation in the market dynamics of a series of dimensions that were a priori alien to it 14 . Today, environment, health and social exclusion 12. A survey published in the New York Times showed that "88 % of consumers are more likely to buy from a company that is socially responsible" [START_REF] Smith | Corporate Citizens and Their Critics[END_REF]; another survey, issued in USA Today, confirmed this result: "76 % of consumers would switch brands or stores that show concern about the community" [START_REF] Jones | Good Works, Good Business[END_REF] (references quoted in [START_REF] Maignan | Corporate Citizenship: Cultural Antecedents and Business Benefits[END_REF]. These attitudes do not concern only American consumers, but can also be observed in Europe: a French survey of the CREDOC conducted in mars 1996 established that the percentage of consumers preoccupied with the "humanitarian quality" of products moved from 40 % to 54 % over a three year period. At the same time, another survey of the Centre Régional de la Consommation (CRC) observed that 71 % of the surveyed persons would accept to pay more for a product if they had the certainty that it was made without children exploitation (http://www.crc-conso.com/etic/default.htm). If we add to this series of facts the older success of "ethical" financial products which today represent 10 % of American financial market and grow faster than the remai ning part of this market [START_REF] Capron | Grandes et petites manoeuvres autour de l'éthique d'entreprise[END_REF], and if we replace social standardization in the general movement for «corporate citizenship» [START_REF] Maignan | Corporate Citizenship: Cultural Antecedents and Business Benefits[END_REF] , one can bet that the move towards social standardization is more a fundamental trend than an epiphenomenon. 13. See the first "Seminar on political consumerism" (Michele Micheletti, ed.) held at City University of Stockholm, May 31-June 2, 2001 (http://www.cityuniv.se/polcon/) and Michele Micheletti's book on the subject (Micheletti, forthcoming).

14. Let us note that the WTO sat up a Committee of Trade and Environment, while the same institution had always refused to institute a similar group on the "fundamental labor standards" (Siroën, 1998, p. 58). The greater advancement of the environment file may be explained by the closest proximity between environmental issues and industrial and objective matters which WTO is more used to deal with, compared to human and social problems that have always embarrassed it and being rejected as ILO's responsibility. But the growing hybridization between technical and social matters and the proliferation of "haired objects" resulting from it (Latour, forthcoming) makes the move from objects to social to labor more and more difficult to avoid. matters are at the heart of economic issues [START_REF] Capron | Grandes et petites manoeuvres autour de l'éthique d'entreprise[END_REF]. Numerous empirical studies converge to show to what extent, since the sixties, the actors of the liberal and capitalist world have found the ways to "internalize externalities", to "frame" the "overflowing" (Callon, 1998), and to allow capitalism to borrow from the arguments of its own critics in order to transform and renew itself (Boltanski & Chiappello, 1999). In many respects, the secular social embeddedness of markets [START_REF] Granovetter | Economic Action and Social Structure: The Problem of Embeddedness[END_REF] is now complemented by a symmetrical movement of economical commitment of societal issues. At the same time, it is difficult to understand this move towards the internalization of externalities without seeing that it relies less on a general transformation of the "spirit of capitalism" than on the progressive development of local techniques, devices and know-hows which mostly have a very loose relationship with the ideologies, doctrines and actors of the "big bad capital". To put it differently, it is not capitalism which digests its critique, it is society itself; it is the coalition of "stakeholders": industry captains, managers, experts, unionists, consumers-all the actors whose interaction produces the emergence of common solutions [START_REF] Capron | Grandes et petites manoeuvres autour de l'éthique d'entreprise[END_REF].

The enrollment of the consumer in this move is absolutely crucial. For a century managers have never stopped claiming that the consumer is king (Cochoy, 1999;[START_REF] Neuville | Le marché et la convention à l'épreuve de l'organisation[END_REF]. It is thus time to remind them of their commitment and to set up procedures designed to show them who is (or who should be) their master (and also to educate the king in order to enlighten and redirect his goodwill). This is how the advocates of "ethics on labels" understand their own cause, for instance when a representative of this group notes: Any means goes. Today, if one takes into account how ultraliberalism is deeply rooted in our society, one discovers that any political action is very difficult to forward. The only means to push things forward is to use the lever that the consumer represents. (quoted in [START_REF] Grenouillet | Fair trade and free trade: état des lieux[END_REF].

In order to understand the standardization of work and the implications of its globalization, it i s necessary to become aware that such processes rely both on the strategic opportunities this type of standardization provides to actors of the capitalist world and, on the other hand, on the possibilities opened by the sharing of decisions between a host of participants.

As far as the first point is concerned, it is clear that social standardization conveys strategic opportunities that go far beyond the ethical virtues it puts forth. Just as the standardization of products defines circulation spaces reserved to standardized products, the standardization of labor could circumscribe clubs of companies and labor groups that would control the access to the global market. This process will happen to the detriment of all those who would not be able to keep up with the required standards and thus would be condemned to remain out of the game. Of course, from a general standpoint, social standards have an immense advantage: by directing competition on job and product quality, rather than on cost and price reduction, they provide a welcome alternative to the employment policies aiming at wage cuts and labor flexibility... a kind of policies that have finally endangered the very foundation of our a dvanced societies (Lallement, 2001;[START_REF] Visser | Du "keynésianisme" à la "troisième voie" : relations du travail et politique sociale en Europe de 1950 à 2000[END_REF], through the deepening of social inequalities, social struggles, job casualness and poverty. Social standards, by counteracting such processes, are of a prominent interest for multinational companies, consulting agencies, but also for workers [START_REF] Barbier | French Public Employment Policies And Human Resources Management Practices: Some Lessons[END_REF] and consumers (Cochoy, 2001) of advanced countries:

The labeling of [the "moral" quality of goods and services] could help us to restore the comparative advantage of deve loped countries in productions with a high labor content. If the (total or partial) eviction of non-labeled varieties (of bad moral quality) succeeds, it is to the detriment of the developing countries and to the advantage of industrial countries which have an obvious comparative advantage in the manufacturing of products of high moral quality (Siroën, 1998, p. 62).

The standardization and the certification of work cumulates two advantages. Firstly, the promotion of the ethical content of goods provides a comparative advantage standing against almost two centuries of job protection and codification in the concerned countries; secondly, the setting of job standards provides a managerial advantage which a century of standardization, quality management and auditing skills ended up reserving to the same countries.

However-and here comes the second point-, the process relies on the promotion of ethical values which are hard to condemn, it brings together groups with various interests where each one will recognize at least a cause he supports, and it also relies on network externalities carrying mechanisms of irreversibility [START_REF] David | Clio and the Economics of QWERTY[END_REF]. Of course, bringing principles into facts is in urgent need. It is necessary to act so that all those who could participate or at least be represented join the standard setting institutions, committees and procedures, enlarge the "hybrid forums" of today [START_REF] Callon | Exploration des débordements et cadrage des interactions: la dynamique de l'expérimentation collective dans les forums hybrides[END_REF], and take their part in the building of the common world (Latour, forthcoming) 15 . From this point of view, the absence of government, of official standardization bodies and of less developed countries in the setting of the SA 8000 standard should be corrected, in order to avoid the risks of any form of standardization taking place in "private consortia" [START_REF] Hawkins | Vers une évolution ou vers une disparition de la "démocratie technique"?[END_REF] 16 . In other words, it is necessary to fight within the 15. Callon and Latour have shown that in order to solve problems in situation of radical uncertainty, such as the mad cow crisis, the OGM controversy or the heating of the atmosphere, new public arenas of discussion are emerging. In these "hybrid forums", politicians, experts, scientists but also activists groups and the general public meet together, on an equal basis, in order to find common solutions. The Kyoto conference is a good example of such a forum and process. 16. A "private consortium" is a group of industrial partners who meet in order to set up their own standardized solutions, objects or services (for instance a protocol for communication technologies) without the participation of the public, of the official standardizing bodies, or of the State agencies. According to Hawkins, avoiding public and political control and participation in the setting of standards jeopardizes the development of a "technical democracy". globalization process rather than against it. Globalization is a type of machine which is designed to move forward but also to exclude. Consequently, it's probably better to step in and to go behind the wheel in order to choose the right direction or to slow down if necessary, instead of remaining on the side of the road, shouting and running, at the risk of being passed, if not run over.

http://www.crc-conso.com/etic/default.htm

Here we discover the historical movement of product qualification: the anonymous product of classical economics was first replaced by the brand's responsibility, then the branded product was guaranteed by standards and certificates, whose advantage is to introduce the impartial viewpoint of a third party[START_REF] Cochoy | L'âne de Buridan revisité: l'homme économique moderne entre marketing et normalisation des produits[END_REF].

For an excellent analysis of this issue, see Isabelle Daugareilh contribution in this book.

It is important to notice that this environmental dimension is itself coupled with the history of quality through the ISO 14000 Standard. For additional information on this point, see[START_REF] Reverdy | L'invention du management environnemental, extension de la qualité industrielle et régulation négociée de l'environnement[END_REF]