Craig Lyon
email: craigl@tirf.ca

Dan Mayhew
email: danm@tirf.ca

Marie-Axelle Granié
email: marie-axelle.granie@univ-eiffel.fr

Robyn Robertson
email: robynr@tirf.ca

Ward Vanlaar
email: wardv@tirf.ca

Heather Woods-Fry
email: heatherw@tirf.ca

Chloé Thevenet
email: chloe.thevenet@univ-eiffel.fr

Gerald Furian
email: gerald.furian@kfv.at

Aggelos Soteropoulos
email: aggelos.soteropoulos@tuwien.ac.at

Katrien Torfs

Huong Nguyen

Keywords: young, elderly, self-report, behaviour, Attitudes, beliefs young, elderly, self-report, behaviour, attitudes, beliefs

The existing literature on young and elderly drivers indicates that they have the highest crash risks compared to other age groups of drivers. This study improves our understanding of the risk factors contributing to young and elderly drivers' elevated crash risk by examining self-report data from the E-Survey of Road User's Safety Attitudes (ESRA). The primary objective of this study is to compare the attitudes and behaviours of young, elderly, and middle-age drivers in Canada, the United States, and Europe. The main focus is on the practice of driving while distracted by mobile phones and driving while fatigued, as these are two dangerous behaviours that demonstrate the impact age may have. The analyses consistently showed that there are differences in the responses attributable to age. In all regions, drivers aged 18-21 years consistently reported higher rates of distracted and fatigued driving and higher rates of perceived social and personal acceptability of these behaviours than drivers aged 35-54 years. Elderly drivers aged 65+ years reported even lower rates of these behaviours and acceptability. Young drivers were also the least likely to believe that distraction and fatigue are frequent causes of road crashes, while elderly drivers were the most likely to believe this. This pattern with respect to age repeats in the support for policy measures as well; young drivers are least likely to support zero tolerance policies for mobile phone use when driving, while elderly drivers are the most likely to support this measure. Multivariate logistic regression modeling confirmed that elderly drivers were the least likely to engage in the use of mobile phones while driving or driving while fatigued. Statistically significant results showed that the middle-age group was less likely than young drivers to read a text message/email or check social media while driving and driving while fatigued.

Introduction

Young and elderly drivers have the highest crash risk compared to other age groups of drivers. In literature, this age-based pattern of crash risk is described as a U-shaped curve and has been shown to be most pronounced for young and elderly drivers when crash risk is measured for fatal crashes or motor vehicle fatalities per distance driven [START_REF] Baldock | Older drivers: Crash involvement rates and causes[END_REF][START_REF] Kostyniuk | Safe mobility of older drivers: concerns expressed by adult children, Top[END_REF][START_REF] Evans | Risks older drivers face themselves and threats they pose to other road users[END_REF][START_REF] Massie | Traffic accident involvement rates by driver age and gender[END_REF][START_REF] Regev | Crash risk by driver age, gender, and time of day using a new exposure methodology[END_REF]. In 2017 in the United States, for example, drivers age 16-19 and drivers age 85 and over had per vehicle mile fatal crash rates of 4.7 and 7. [START_REF]Older drivers[END_REF], respectively compared to a rate of only 1.4 fatal crashes per 100 million miles traveled for those age 45-49 [START_REF]Older drivers[END_REF].

This study improves our understanding of the risk factors contributing to young and elderly drivers' elevated crash risk by examining self-report data from the E-Survey of Road User's Safety Attitudes (ESRA; www.esranet.eu). The ESRA project is a joint initiative of road safety institutes, research organisations, public services, and private sponsors, aiming at collecting comparable (inter)national questionnaire-based data on road users' opinions, attitudes, and behaviour with respect to road traffic risks. The ESRA database enables a wide range of analyses that are useful for understanding road safety risks of young and elderly drivers and the effectiveness of measures to reduce their risk.

The primary objective of this study is to compare the attitudes and behaviours of young, elderly, and middle-age drivers in Canada, the United States, and Europe. The main focus will be on the influence of driving while distracted by mobile phones and driving while fatigued, as these are two dangerous behaviours that demonstrate the impact age may have.

Literature Review

Young and elderly drivers are at elevated crash risk, but for different reasons. The literature clearly establishes that young drivers do not have enough driving experience to fully develop the skills needed to identify and safely respond to hazards on the road [START_REF] Fisher | Handbook of Teen and Novice Drivers: Research, Practice, Policy and Directions[END_REF][START_REF] Harrison | The Role of Experience in Learning to Drive: A theoretical discussion and an investigation of the experiences of learner drivers over a two-year period[END_REF][START_REF] Mayhew | New to the road. Young drivers and novice drivers: Similar problems and solutions? Traffic Injury Research Foundation[END_REF][START_REF] Mayhew | The safety value of driver education and training[END_REF][START_REF] Twisk | Trends in young driver risk and countermeasures in European countries[END_REF]. Additionally, youthfulness also contributes to elevated crash risk [START_REF] Mccartt | Effects of age and experience on young driver crashes: review of recent literature[END_REF][START_REF] Mcdonald | Simulated driving performance, self-reported driving behaviors, and mental health symptoms in adolescent novice drivers[END_REF]. Certain biological, mental, and developmental changes during adolescence contribute to young drivers having a disproportionate crash rate. The key factors include overconfidence, sensation seeking, widespread sleep deprivation and fatigue, peer influences to engage in risky driving behaviours, and intentional risky driving behaviours, such as speeding, tailgating, distracted driving, and fatigued driving [START_REF] Bates | Factors contributing to crashes among young drivers[END_REF][START_REF]Older drivers[END_REF][START_REF] Halpern-Felsher | Handbook of Teen and Novice Drivers : Research, Practice, Policy, and Directions[END_REF][START_REF]Organisation for Economic Co-operation and Development (OECD), Young Drivers: The Road to Safety[END_REF][START_REF] Scott-Parker | A further exploration of sensation seeking propensity, reward sensitivity, depression, anxiety, and the risky behaviour of young novice drivers in a structural equation model[END_REF][START_REF] Tefft | Teen driver risk in relation to age and number of passengers, United States, 2007-2010[END_REF].

The literature also clearly establishes that like young drivers, elderly drivers have a high crash risk owing to ageing-related factors-primarily, deteriorating motor, perceptual and cognitive skills critical for driving safely [START_REF] Baldock | Older drivers: Crash involvement rates and causes[END_REF][START_REF]Organisation for Economic Co-operation and Development (OECD), Young Drivers: The Road to Safety[END_REF][START_REF] Clarke | Older drivers' road traffic crashes in the UK[END_REF][START_REF] Mayhew | Driver education and graduated licensing in North America: Past, present, and future[END_REF]. Additionally, lifestyle factors including chronic health problems and the side effects of medications also contribute to elderly drivers' crashes. Furthermore, the increasing frailty of elderly drivers makes them more likely to be seriously injured or killed in a collision than young drivers. They also restrict their driving and drive fewer miles than young and middle-age drivers, often in urban areas that place them at higher crash risk, especially at intersections [START_REF] Baldock | Older drivers: Crash involvement rates and causes[END_REF][START_REF] Clarke | Older drivers' road traffic crashes in the UK[END_REF][START_REF] Mayhew | Driver education and graduated licensing in North America: Past, present, and future[END_REF][START_REF] Rakotonirainy | Older drivers' crashes in Queensland, Australia[END_REF]. These frailty and low-mileage biases, in part, explain the elevated risk of fatal crashes and serious injuries when rates are calculated per miles driven.

Although young and elderly drivers have an elevated crash risk for different reasons, they also share a few risk factors, such as distracted driving and fatigued driving [START_REF] Groeger | Youthfulness, inexperience, and sleep loss: the problems young drivers face and those they pose for us[END_REF][START_REF] Fofanova | Distraction while driving: The case of older drivers[END_REF][START_REF] Horrey | Attention Allocation and Maintenance in Novice and Teen Drivers[END_REF][START_REF] Paterson | Fatigue and Rad Safety for Young and New Drivers[END_REF][START_REF] Thompson | Distracted driving in elderly and middle-age drivers[END_REF]. However, there are also important differences in the distracted and fatigued driving behaviours of young and elderly drivers. Research has shown that both young and elderly drivers are negatively affected by distractions while driving, although elderly drivers engage in distracting tasks less than young and middle-age drivers. Additionally, young drivers are more frequently observed to be manipulating handheld (HH) devices than elderly drivers [START_REF] Woods-Fry | Comparison of self-declared mobile use while driving in Canada, the United States, and Europe: results from the European survey of road users' safety attitudes[END_REF][START_REF] Caird | A Review of Novice and Teen Driver Distraction[END_REF][START_REF]Mobile Phone Use: A Growing Problem of Driver Distraction[END_REF]. Young and elderly drivers have been found to be more adversely impacted by secondary tasks than middle-age drivers. Visual-manual distractions impact drivers of all ages, but cognitive distraction may have a larger impact on young drivers [START_REF] Guo | The effects of age on crash risk associated with driver distraction[END_REF]. Fatigue is a risk factor for all drivers [START_REF] Vanlaar | Fatigued and drowsy driving: A survey of attitudes, opinions and behaviours[END_REF][START_REF] Ncsdr/Nhtsa | Expert panel on driver fatigue and sleepiness: drowsy driving and automobile crashes[END_REF][START_REF] Owens | Prevalence of Drowsy Driving Crashes: Estimates from a Large-Scale Naturalistic Driving Study[END_REF]. Even though young and elderly drivers drive while fatigued, research has shown that young drivers are likely to be fatigued after midnight into the early morning hours, while elderly drivers are more likely to be fatigued in the afternoon [START_REF] Brown | Prospects for technological countermeasures against driver fatigue[END_REF][START_REF] Obst | Age and gender comparisons of driving while sleepy: Behaviours and risk perceptions[END_REF][START_REF] Summala | Young driver accidents: Risk taking or failure of skills?[END_REF].

Understanding such similarities and differences in risk factors of young and elderly drivers is critical to developing effective policies and programs to reduce their elevated crash risk. Previous surveys have attempted to explore age-related factors in distracted and fatigued driving. Survey data from the United States indicated that drivers aged 65+ years have the lowest rates of mobile phone use (call, text, or apps), while drivers aged 20 years or younger do not have the highest rates for these behaviours, and the highest rates are between the ages of 21 to 54, depending on the question asked [START_REF] Schroeder | National survey on distracted driving attitudes and behaviors -2015[END_REF]. An Australian survey [START_REF] Mcevoy | The impact of driver distraction on road safety: results from a representative survey in two Australian states[END_REF] found that younger drivers (aged 18-30 or 18-49 years depending on the question posed) were more likely to report distracting activities while driving and rated distracting activities to be significantly less risky than elderly drivers. Drivers aged 18-30 years were also more likely to report a crash due to distraction. A survey on fatigued driving in Europe found that the odds of falling asleep at the wheel were significantly higher in drivers under the age of 70 years compared to those over 70 years [START_REF] Goncalves | Sleepiness at the wheel across Europe: a survey of 19 countries[END_REF]. Data from the first ESRA survey conducted in 2015 [START_REF] Trigoso | Distraction and fatigue, ESRA thematic report no. 3. ESRA project (European Survey of Road users' safety Attitudes)[END_REF] found that the percentage of mobile phone use while driving was particularly high among drivers up to 34 years old and fatigued driving was also more prevalent in this age group. This study extends on this earlier work by using data from the more extensive ESRA survey conducted in 2019 to examine distracted driving and fatigued driving behaviours of young and elderly drivers. It also contributes to the field by using common measures to allow for direct comparisons between young and elderly driver behaviour in different geographic regions. This better informs our understanding of where similarities and differences exist in distracted and fatigued driving behaviour across age groups and regions as findings from a previous study in only one country may not necessarily apply to another. For example, the finding from one country that young drivers are more likely to report specific distracted driving activities than elderly drivers may not extrapolate to other countries that differ culturally, politically, economically, and in terms of road safety policy and program development. The ESRA survey results in this study pose the same questions to young and elderly drivers from different countries so the knowledge and insights gained from this research are directly applicable to all of the countries in the investigation, which facilitates direct international comparisons.

Methodology

The ESRA project is a joint initiative of research organizations and road safety institutes all over the world. The aim is to collect comparable national data on road users' opinions, attitudes, and behaviour with respect to traffic and road safety, and to provide policy makers with data to inform policy measures. The themes covered include self-declared behaviour, attitudes and opinions on unsafe traffic behaviour, enforcement experiences, involvement in road crashes, and support for policy measures. The survey addresses different road safety topics (e.g., driving under the influence of alcohol, drugs and medicines, speeding, distraction) and targets different types of road users. The second ESRA survey (ESRA2) was conducted in 32 countries, including Canada (n = 602 drivers), the United States (n = 595 drivers), and Europe (n = 14,250 drivers), which are the focus of this paper. The focus was laid on these countries because they are similar in terms of being western, developed and industrialized. In general, there are similarities in the driver licensing processes and traffic environments in North America and Europee.g., learners have to practice driving under supervision of a parent/guardian and/or driver trainer, and pass knowledge and road tests before they can obtain a driver's licence; there are roundabouts to control traffic, and a mix of road types, including two-lane highways, residential streets, and expressways/freeways. However, there are also important differences across and even within these countries in terms of culture, politics, demographics, economics, and traffic safety laws, programs and policies. For example, Canada and the United States generally have a younger driver licensing age than in Europe (16 years old versus 17 or 18 years old) and all jurisdictions in North America have some form of graduated driver licensing (GDL) system, which is not the case in Europe, although the features of GDL differ across U.S. states and Canadian provinces. Traffic safety laws and penalties regarding, for example, cell phone use when driving and driving fatigued also differ across and within these countries.

The ESRA2 survey is a web survey using access panels coordinated by the Vias Institute in Belgium (www.vias.be) with a core group of partner organisations from 11 countries. The target population was the adult population (≥18 years) of each country. The targeted number of respondents was 1,000 in each country, with at least 600 respondents being regular car drivers. If needed, the sample of 1,000 respondents could be extended in order to fulfill both the aforementioned requirements. Twenty individual countries were included in the European region (list of countries available on www.esranet.eu). The total sample size consisted of more than 35,000 road users from 32 countries with just over 30,000 of those holding a driving license or learner's permit. Hence, the ESRA2 database is a comprehensive dataset, which enables a wide range of analyses useful for understanding road safety risks and the effectiveness of measures. Further details on the design and administration of the survey are available in a separate article in this special issue.

In view of comparability, not just between the countries but also with past surveys, almost all questions of the ESRA2 survey were based on, and often identical to, questions previously used and validated in Belgian [START_REF] Meesmann | Appendix Methodology & Questionnaire. Results of the BIVV/IBSR three-yearly road safety attitude survey[END_REF]42), European [START_REF] Cestac | The SARTRE 4 Survey: European Road Users' Risk Perception and Mobility[END_REF], and American [START_REF]Traffic Safety Culture Index[END_REF] surveys. The survey covered diverse themes in varying detail due to survey duration constraints (all information on the questionnaire is available on www.esranet.eu). The questionnaire was produced in 30 different country-language versions. The translated versions were reviewed by the ESRA team to ensure consistency and concept validity within each language. Data collection took place in two waves in 2018 and 2019.

Table 1 shows the distribution of the full sample used per region. The questions related to driver behaviour in the last 30 days were only posed to respondents who reported driving a car at least a few times a month, while all other questions were posed to all respondents. In the first part of our analysis, we reported descriptive results of the three regions for several aspects: self-declared behaviours, acceptability (personal and social), risk perception, and support for policy measures. Most of the questions of the survey were presented on Likert scales, which were dichotomized for the analysis. Description of the scales and correspondent dichotomization is discussed in the results. For this first set of analyses, responses are tested for statistically significant differences with respect to the age categories. Three age categories were considered. The participants between the ages of 18 and 21 were considered young drivers and above 65, elderly drivers. For comparison, participants between the ages of 35 and 54 were considered middle-age drivers. Weighting of the data was done taking into account small corrections with respect to representativeness of the sample based on gender and the three age groups (18-21, 35-54, 65+) using population statistics from the United Nations data [45]. The weights were determined separately for each region and determined by dividing the proportion of each age/gender category in the population by the proportion in the survey sample. Due to the ordinal nature of the data, the chi-square test for independence was used to assess if the observed differences were statistically significant. The strength of the association between variables was assessed using Cramer's V coefficient. These tests indicate if age is a significant factor overall and do not compare each age group to all others.

In the second part, we carried out multivariate analyses, investigating factors predicting selfdeclared behaviours. The predictive factors included in this analysis were relevant because previous research had shown that one or more of these factors (e.g., age, gender, amount of driving) contributed to explaining distracted driving and fatigued driving behaviours. Binary logistic regression models were used to investigate the association between several explanatory variables, including age and self-declared behaviours. Note that the data were also weighted in the same manner as the descriptive analyses.

Results

Descriptive analysis

The respondents surveyed in each region were asked questions about distraction from mobile phone use and driving while fatigued. The results are grouped into several sections: self-declared behaviours in traffic, acceptability of unsafe traffic behaviours, attitudes toward safe and unsafe traffic behaviours, risk perception, and support for policy measures.

Self-declared behaviours in traffic

Rates of self-declared handheld mobile use, hands-free mobile use, sending or reading a text message or checking social media, and driving while fatigued at least once within the last 30 days are reported by region in Table 2. All questions were answered on a Likert scale from 1 (never) to 5 (almost always). The percentages of 'at least once' (answers 2 to 5) and the 95 th percentile confidence intervals (CIs) are presented in the results along with the p-value for the chi-squared statistical test of differences between age groups and with the corresponding value of Cramer's V.

In all regions, the young age category of 18-21 years reported the highest proportion of respondents engaging in behaviours related to distraction and fatigue, and the elderly age category of 65+ years reported the lowest proportion. These differences by age group of the reported proportions are all statistically significant at the 95 th percentile level or better.

In all three regions, the largest differences by age category, as measured by Cramer's V, were in reading a text/email or consulting social media while driving. The proportions of young and elderly drivers reporting this behaviour were 63.6% and 28.1% in Canada, 62.8% and 30.4% in the United States, and 62.9% and 35.4% in Europe, respectively. In the United States and Europe, the smallest differences by age category as measured by Cramer's V, were found for driving when one is so sleepy that it is difficult to keep one's eyes open. In the United States, the proportions were 54.4% and 28.4% for young and elderly drivers, respectively, and 54.1% and 38.3% in Europe. In Canada, the smallest difference by age category was found for hands-free cell phone conversations while driving, where the proportions for young and elderly drivers were 63.6% and 48.1%, respectively. Cramer's V 0.17 0.15 0.08

Acceptability of safe and unsafe traffic behaviours

Rates of the perceived social acceptability of handheld mobile use and sending or reading a text message/checking social media; personal acceptability of handheld mobile use, hands-free mobile use, sending or reading a text message/checking social media, and fatigued driving are reported by region in Table 3. All questions were answered on a Likert scale from 1 (unacceptable) to 5 (acceptable). The percentages of acceptability (answers 4 or 5) are shown in the results with 95 th percentile confidence intervals (CIs), the p-value for the chi-squared statistical test of differences between age groups, and the corresponding value of Cramer's V.

When asked how acceptable most other people would say it is to talk on a handheld mobile phone while driving, or to read a text message/email or check social media while driving, the young drivers reported the highest rates of perceived social acceptability and elderly drivers, the lowest in all regions. These differences by age group of the reported proportions are all statistically significant at the 95 th percentile level or better. The magnitude of the impact of age on responses as measured by Cramer's V is similar for the two behaviours. The largest difference between the two behaviours was in the United States, where 38.0% of the younger drivers reported social acceptability for talking on a handheld mobile phone while driving, and 16.4% reported so for the reading of a text message/email or checking social media while driving.

When asked if they felt it was personally acceptable to talk on a handheld phone, talk on a handsfree phone, read a text message/email, or check social media while driving or to drive when so sleepy that they have trouble keeping their eyes open, the young drivers reported the highest rates and elderly drivers, the lowest in all regions. The differences by age category in Canada and the United States as measured by Cramer's V are notable, ranging from 0.11 to 0.31. In contrast, in Europe, the differences are smaller, ranging from 0.07 to 0.13.

Beliefs concerning risk perception

The respondents were asked how often they thought risky behaviours caused a road crash involving a car. Several items were asked including using a handheld phone while driving, using a hands-free phone while driving and driving while fatigued. The scale of answers ranged from 1 (never) to 6 (almost always). The percentages of often/frequently (answers 4 to 6) are shown in the results by region in Table 4.

For using a handheld phone while driving, in the United States and Europe, young drivers reported the lowest rates of agreement and elderly drivers, the highest. In Canada, the middle-age group reported the lowest rate of agreement (69.7%), while the young age group and elderly age group reported 77.8% and 87.4%, respectively. For using a hands-free phone while driving, in the United States and Europe, young drivers again reported the lowest rates of agreement and elderly drivers, the highest. In Canada, the percentages of the young and middle-aged groups were roughly equal at 50.9% and 49.7%, respectively. The elderly age group reported the highest rate of agreement (65.8%). For fatigued driving, young drivers reported the lowest rates of agreement and elderly drivers, the highest in all regions. Cramer's V 0.12 0.13 0.11

Support for policy measures

By asking the participants to answer "Do you support or oppose a legal obligation to have zero tolerance for using any type of mobile phone while driving for all drivers?," the support for policy measures was assessed. The question was answered on a Likert scale from 1 (oppose) to 5 (support). The percentages of 'support' (answers 4 to 5) are presented in Table 5.

In the United States and Europe, young drivers reported the lowest rates of support and elderly drivers, the highest. In Canada, the percentages of the young and middle-age groups were roughly equal at 58.8% and 56.9%, respectively. The elderly age group reported the highest rate of support (78%).

Multivariate analysis

Four dependent variables were selected for further analysis: self-declared behaviour in the last 30 days for talking on a handheld mobile phone, talking on hands-free mobile phone, reading a text message/email or checking social media, and driving when so sleepy that they had trouble keeping their eyes open.

For each behaviour, logistic regression models were estimated to study the association between a set of explanatory variables and the reported behaviour. For each model, the dependent variable is binary, and indicates the absence (0 = never) or presence (1 = at least once) of the self-declared behaviour within the past 30 days. Demographics (region, gender, age, and education level), frequency of driving, and the perceived social and personal acceptability of unsafe traffic behaviour, risk perception, and support for road safety measure were treated as the explanatory variables where available. Odds ratios (ORs) and 95% confidence intervals (CIs) were used to estimate the strength of the relationship between these explanatory variables and the reported behaviours. All results are presented in Table 6. The reference categories are listed in brackets following each independent variable in the model.

Factors predicting self-declared talking on a handheld mobile device while driving

Compared to drivers in the age group 18-21 years elderly drivers were 56% less likely to report this behaviour (OR = 0.44; 95% CI: 0.39-0.49; p < 0.01). Handheld mobile use was also associated with respondents' gender, as female drivers were 24% less likely to report talking on a handheld mobile while driving, in comparison with male drivers (OR = 0.76; 95% CI: 0.69-0.83; p < 0.01). In comparison with those who drove only a few days a month, individuals who reported a driving frequency of at least a few days a week were 77% more likely to talk on a handheld device while driving (OR = 1.77; 95% CI: 1.48-2.12; p < 0.01). Those who felt that it was socially acceptable to talk on a handheld device while driving were 79% more likely to report having performed this behaviour (OR = 1.79; 95% CI: 1.48-2.16; p < 0.01). Those who personally felt that it was acceptable to talk on a handheld device while driving were 262% more likely to report having performed this behaviour (OR = 3.62; 95% CI: 2.70-4.86; p < 0.01). How drivers perceive the risk of handheld mobile use also impacts the reported behaviour. Those who reported that handheld mobile use is often a factor in road crashes were 25% less likely to report having performed this behaviour (OR = 0.75; 95% CI: 0.67-0.83; p < 0.01). Drivers with zero tolerance to using any type of mobile phone while driving were 49% less likely to have reported talking on a handheld mobile phone while driving (OR = 0.51; 95% CI: 0.47-0.56; p < 0.01).

Factors predicting self-declared talking on a hands-free mobile device while driving

Compared to drivers in the age group 18-21 years elderly drivers were 35% less likely to report this behaviour (OR= 0.65; 95% CI: 0.58-0.72; p < 0.01). Hands-free mobile use was also associated with respondents' gender, as female drivers were 23% less likely to report talking on a hands-free mobile while driving, in comparison with male drivers (OR= 0.77; 95% CI: 0.71-0.84; p < 0.01), a result similar to that for handheld use. In comparison with those who only drove a few days a month, individuals who reported a driving frequency of at least a few days a week were 78% more likely to talk on a hands-free device while driving (OR = 1.78; 95% CI: 1.44-2.21; p < 0.01). Those who personally felt that it was acceptable to talk on a hands-free device while driving were 149% more likely to report having performed this behaviour (OR = 2.49; 95% CI: 2.24-2.77; p < 0.01). How drivers perceive the risk of hands-free mobile use also impacts the reported behaviour. Those who reported that hands-free mobile use is often a factor in road crashes were 22% less likely to report having performed this behaviour (OR = 0.78; 95% CI: 0.71-0.85; p < 0.01). Drivers with zero tolerance to using any type of mobile phone while driving were 50% less likely to have reported talking on a hands-free mobile phone while driving (OR = 0.50; 95% CI: 0.45-0.55; p < 0.01).

Factors predicting self-declared use of text message/email/social media while driving

When comparing drivers in the age group 18-21 years with those aged 35-54 years, the likelihood of drivers reporting the use of text message/email/social media while driving increased by 59% when controlling for all other factors (OR = 1.59; 95% CI: 1.35-1.86; p < 0.01). For drivers aged 65+, these odds decreased by 75% (OR = 0.25; 95% CI: 0.22-0.30; p < 0.01). Use of text message/email/social media was associated with respondents' gender, as female drivers were 16% less likely to report this behaviour (OR= 0.84; 95% CI: 0.76-0.33; p < 0.01). In comparison with those who only drive a few days a month, individuals who reported a driving frequency of at least a few days a week were 51% more likely to report doing so (OR = 1.51; 95% CI: 1.21-1.89; p < 0.01). Those who felt that it was socially acceptable to use text message/email/social media while driving were 92% more likely to report having performed this behaviour (OR = 1.92; 95% CI: 1.47-2.50; p < 0.01). Those who personally felt that it was acceptable to do so were 601% more likely to report having performed this behaviour (OR = 7.01; 95% CI: 3.11-15.83; p < 0.01). How drivers perceive the risk of text message/email/social media use also impacts the reported behaviour. Those who reported that this behaviour is often a factor in road crashes were 24% less likely to report having performed this behaviour (OR = 0.76; 95% CI: 0.68-0.85; p < 0.01). Drivers supportive of zero tolerance of using any type of mobile phone while driving were 48% less likely to have reported this behaviour while driving (OR = 0.52; 95% CI: 0.47-0.57; p < 0.01).

Factors predicting self-declared driving while sleepy

When comparing drivers in the age group 18-21 years to those aged 35-54 years, the likelihood of drivers reporting driving while sleepy increased by 46% when controlling for all other factors (OR = 1.46; 95% CI: 1.24-1.73; p < 0.01). For drivers aged 65+, these odds decreased by 47% (OR = 0.53; 95% CI: 0.47-0.60; p < 0.01). Driving while sleepy was associated with respondents' gender, as female drivers were 42% less likely to report this behaviour (OR= 0.58; 95% CI: 0.53-0.64; p < 0.01). In comparison with those who only drive a few days a month, individuals who reported a driving frequency of at least a few days a week were 57% more likely to report doing so (OR = 1.57; 95% CI: 1.29-1.90; p < 0.01). Those who personally felt that it is acceptable to drive while sleepy were 445% more likely to report having performed this behaviour (OR = 5.45; 95% CI: 3.46-8.58; p < 0.01). How drivers perceive the risk of driving while sleepy also impacts the reported behaviour. Those who reported that this behaviour is often a factor in road crashes were 21% less likely to report having performed this behaviour (OR = 0.79; 95% CI: 0.71-0.89; p < 0.01).

Discussion

The objective of this study was to examine and compare the rates of self-reported behaviours, beliefs, and attitudes related to distracted driving due to mobile phone use and driving while fatigued among young, elderly, and middle-age drivers. Analyses were conducted using self-report data from Canada (n = 602), the United States (n = 595), and Europe (n = 14,250).

The analyses consistently showed that there are differences in the responses attributable to age. The magnitude of the effects as measured by Cramer's V tended to be the smallest in Europe, while the largest effects were found in Canada or the United States depending on the question asked. In all regions, young drivers aged 18-21 years consistently reported higher rates of distracted and fatigued driving and higher rates of perceived social and personal acceptability of these behaviours than drivers aged 35-54 years. Elderly drivers aged 65+ reported even lower rates of these behaviours and acceptability. Young drivers were also the least likely to believe distraction and fatigue to be frequent causes of road crashes, while elderly drivers were the most likely to believe this. This pattern with respect to age repeats in the support for policy measures as well; young drivers are least likely to support zero tolerance policies for mobile phone use while driving, while elderly drivers are the most likely to support this measure.

An analysis was also done to examine the factors impacting four types of self-declared behaviour: talking on a handheld mobile phone, talking on hands-free mobile phone, reading a text message/email or checking social media, and driving when so sleepy that they had trouble keeping their eyes open.

Statistically significant results showed that elderly drivers were the least likely to engage in all four behaviours and the young drivers were more likely than the middle-age drivers to read a text message/email or check social media while driving and driving while fatigued. However, the difference was not significant for handheld and hands-free phone use, once the other variables were controlled. In other words, age has an effect on the reported behaviours of the elderly drivers for the four behaviours studied and for young drivers' use of phone for text messaging or social media and driving while fatigued. For young drivers, it appears that their increased likelihood over middle-age drivers is fully accounted for through attitudes and perceptions of risky behaviour with respect to phone use for conversing while driving. Thus, the effect of age on distraction and fatigue is not fully captured through the attitudes and perceptions measured here for elderly drivers. This is also true for young drivers with respect to texting/social media and fatigue and this needs further investigation.

Female drivers were found to be less likely to engage in all four behaviours. Those who reported perceived social acceptability or personal acceptability for these behaviours were more likely to report having engaged in them. Respondents who reported a belief that these behaviours contribute to crash risk and respondents who support zero tolerance for mobile phone use while driving were less likely to engage in the related behaviour. More frequent driving exposure (at least 4 days a week) increases the likelihood of all four behaviours. It should be noted, however, that because of the larger sample size, the European results are more precise and have more influence on the estimated logistic regression models.

Finally, some statistically significant differences were seen between regions when controlling for all other variables. For handheld mobile use, respondents in Canada were least likely to report this behaviour, followed by Europe and the United States. This means that Canadians are the least likely to report talking on a handheld mobile device while driving. These results are in line with the descriptive analysis in this study and a previous ESRA study [START_REF] Woods-Fry | Comparison of self-declared mobile use while driving in Canada, the United States, and Europe: results from the European survey of road users' safety attitudes[END_REF] showing that Canadian drivers report the lowest proportions of talking on a handheld mobile device, whereas Europeans and Americans report higher proportions of this behaviour. Compared to Canada, respondents from the States were more likely to report the use of text message/email or social media while driving.

Conclusions

The results of this study improve upon our understanding of age-related factors in Europe and North America with respect to driving while distracted by mobile phones and driving while fatigued. Understanding the similarities and differences by age group can inform policies and programs to reduce crash risk. For example, the findings that young drivers aged 18-21 years, especially males, consistently reported higher rates of distracted and fatigued driving and higher rates of perceived social and personal acceptability of these behaviours than older age groups suggest that young male drivers should be the primary target for policies and programs on distracted and fatigued driving. This is the case in Canada, the United States and Europe, the three regions included in this study. Moreover, road safety education efforts on distracted and fatigued driving should focus on reducing the acceptability of these behaviours and better informing young drivers about the associated crash risks as those who believed that these behaviours contributed to crash risk were less likely to engage in them. Research shows that interventions based on road user behaviours in road safety education may improve behavioural outcomes. Positive associations between knowledge of traffic rules, positive attitudes towards road safety and risk perception suggest the need to strengthen these elements in road safety education interventions [START_REF] Alonso | Effect of Road Safety Education on Road Risky Behaviours of Spanish Children and Adolescents: Findings from a National Study[END_REF]. The design of interventions should consider that drivers with high rates of reported stress or physiological stress have been found to have higher rates of both unintentional errors and deliberate transgressions when driving [START_REF] Useche | Risky Behaviors and Stress Indicators between Novice and Experienced Drivers[END_REF].

In the United States more so than in Canada and Europe, safety efforts should focus on encouraging drivers to refrain from using handheld mobile phones because respondents in the United States were most likely to report this behaviour. Although regional differences were apparent in distracted and fatigued driving, there were also similarities in behaviours and associated predictive factors across regions suggesting that in general, new and proven safety measures implemented to better address distracted and fatigued driving in one region may also work in another region despite the fact that these regions differ in many ways, including in traffic safety laws, programs and policies. Additionally, this work demonstrates the use of large-scale survey data to inform the development of road safety policies and programs.

Limitations of the Data

While self-reported survey data are informative, there are some limitations. In general, selfreported survey data are vulnerable to a number of biases, such as [START_REF] Choi | A catalog of biases in questionnaires[END_REF][START_REF] Krosnick | Question and Questionnaire design[END_REF] desirability biasthe tendency of respondents to provide answers that present a favourable image of themselves (e.g., individuals may over-report good behaviour or under-report bad, or undesirable behaviour); bias through misunderstanding of questions (e.g., questions with difficult words or long questions); and recall errorunintentional faulty answers due to memory errors. Despite the advantages of online surveys, the representativeness of the surveyed populations may be a problem, mainly for countries with low rates of internet use. That is, however, unlikely for the countries used in the analyses discussed in this paper.

7 .

 7 01 (3.11-15.83)** Personal acceptability to drive when so sleepy that they have trouble keeping their eyes open 5.45 (3.46-8.58)** Risk Perception (variable equal to 1 if respondent rated risk as 4 to 6 on 6-point scale; Ref. category 0 otherwise) Using a handheld mobile phone while driving is often a factor in road Support for policy measures (variable equal to 1 if respondent rated support as 4 or 5 on 5point scale; Ref. category 0 otherwise) Have zero tolerance for using any type of mobile phone while driving for all drivers 0.51 (0.47-0.56)** 0.50 (0.45-0.55)** 0.52 (0.47-0.57)** Notes: (1)* p-value<0.05, **p-value<0.01.

Table 1 Sample Distribution per Region [frequency, percentage by region]

 1

	Sex	Age			Region
			Europe	Canada	United States
	Male	18-21	641	4.5%	34	5.6%	26	4.3%
		35-54	4,231	29.7%	164	27.2%	166	27.6%
		65+	2,151	15.1%	95	15.8%	90	15.0%
	Female	18-21	562	3.9%	29	4.8%	30	5.0%
		35-54	4,108	28.8%	171	28.4%	173	28.7%
		65+	2,557	17.9%	109	18.1%	110	18.3%
	Total		14,250		602		595
	Note: Sample distribution is unweighted.

Table 2 Self-declared Behaviour [percentage, (95% CI)]

 2

	Question	Age	Canada	United States	Europe
	Talk on handheld	18-21	54.0 (41.7-65.9) 70.0 (56.8-80.6) 59.2 (56.3-61.9)
	mobile phone while driving	35-54	36.6 (31.6-41.9) 54.6 (49.2-59.8) 51.4 (50.3-52.5)
		65+	28.6 (22.8-35.2) 37.5 (31.1-44.5) 40.7 (38.9-42.5
		p-value	0.001	<0.001	<0.001
		Cramer's V 0.15	0.20	0.12

Table 3 Acceptability of Safe and Unsafe Traffic Behaviour [percentage, (95% CI)]

 3

	Question	Age	Canada	United States	Europe
	Social	18-21	25.5 (16.2-37.7)	38.0 (26.2-51.4)	13.2 (11.4-15.3)
	Acceptability -Talk on	35-54	2.7 (1.4-5.2)	13.9 (10.6-18.0)	9.2 (8.6-10.0)
	handheld	65+	1.0 (0.3-3.9)	5.5 (3.0-9.6)	5.2 (4.1-6.5)
	mobile phone while driving	p-value	<0.001	<0.001	<0.001
		Cramer's V	0.35	0.26	0.09
	Social	18-21	23.9 (15.0-36.0)	16.4 (8.7-28.7)	8.6 (7.2-10.4)
	Acceptability -Read a text	35-54	3.0 (1.6-5.5)	5.6 (3.6-8.7)	5.9 (5.4-6.5)
	message/emai	65+	1.0 (0.3-3.9)	2.0 (0.7-5.1)	3.3 (2.4-4.5)
	l or check social media	p-value	<0.001	<0.001	<0.001
	while driving	Cramer's V	0.33	0.18	0.07
	Personal	18-21	19.2 (11.2-30.8)	20.0 (11.4-32.7)	6.5 (5.2-8.0)
	Acceptability -Talk on	35-54	2.1 (1.0-4.4)	8.6 (6.0-12.1)	3.8 (3.4-4.3)
	handheld	65+	0.5 (0.1-3.3)	0.5 (0.1-3.4)	1.0 (0.7-1.3)
	phone while driving	p-value	<0.001	<0.001	<0.001
		Cramer's V	0.31	0.22	0.10
		18-21	38.2 (27.1-50.7)	48.0 (35.2-61.0)	45.9 (43.1-48.8)

Table 4 Risk Perception [percentage, (95% CI)]

 4

	Question	Age	Canada	United States	Europe
	Using a	18-21	77.8 (65.9-86.4)	56.4 (43.2-68.8)	63.8 (61.0-66.4)
	handheld phone while driving	35-54	69.7 (64.6-74.4)	66.0 (60.8-70.9)	73.4 (72.4-74.4)
		65+	87.4 (82.1-91.3)	79.0 (72.8-84.1)	81.4 (80.0-82.8)
		p-value	<0.001	0.001	<0.001
		Cramer's V	0.19	0.16	0.12
	Using a hands-	18-21	50.9 (38.7-63.0)	28.4 (18.1-41.6)	36.1 (33.4-38.9)
	free phone while driving	35-54	(44.4-55.1)	40.4 (35.3-45.7)	46.2 (45.1-47.3)
		65+	65.8 (59.0-72.0)	60.6 (53.6-67.1)	58.5 (56.7-60.3)
		p-value	0.001	<0.001	<0.001
		Cramer's V	0.15	0.22	0.14
	Driving while	18-21	63.5 (50.9-74.4)	56.8 (43.5-69.2)	62.9 (60.1-65.6)
	fatigued	35-54	70.0 (64.9-74.7)	64.9 (59.6-69.8)	73.7 (72.7-74.7)
		65+	79.5 (73.4-84.5)	76.1 (69.7-81.5)	80.0 (78.5-81.4)
		p-value	0.015	0.005	<0.001

Table 5 Support for Policy Measures [percentage, (95% CI)]

 5

	Question	Age	Canada	United States	Europe
	Have zero	18-21	58.8 (46.3-70.2)	36.4 (24.9-49.7)	34.5 (31.9-37.3)
	tolerance for using any type of	35-54	56.9 (51.5-62.2)	48.6 (43.3-53.9)	49.3 (48.2-50.4)
	mobile phone	65+	78.0 (71.8-83.2)	59.5 (52.6-66.1)	62.4 (60.7-64.1)
	while driving for all drivers	p-value	<0.001	0.004	<0.001
		Cramer's V	0.20	0.14	0.16

Table 6 Logistic Regression Models of Self-declared Driver Behaviours Dependent variable: reported behaviour (last 30 days) (0 = never; 1 = at least once) Independent variables (reference categories)

 6

		Handheld	Hands-free	Text	Fatigued
		mobile	mobile	message/email	driving
		phone use	phone use	/social media
		Odds Ratio	Odds Ratio	Odds Ratio	Odds Ratio
		(95% CI)	(95% CI)	(95% CI)	(95% CI)
	Sociodemographic
	Gender (Ref. category male)
	female	0.76 (0.69-	0.77 (0.71-	0.84 (0.76-	0.58 (0.53-
		0.83)**	0.84)**	0.93)**	0.64)**
	Age group (Ref. category 35-54)
	18-21	1.07 (0.91-	0.93 (0.80-	1.59 (1.35-	1.46 (1.24-
		1.25)	1.09)	1.86)**	1.73)**
	65+	0.44 (0.39-	0.65 (0.58-	0.25 (0.22-	0.53 (0.47-
		0.49)**	0.72)**	0.30)**	0.60)**
	Region (Ref. category Canada)
	Europe	1.96 (1.53-	1.08 (0.89-	1.07 (0.85-	1.17 (0.92-
		2.51)**	1.32)	1.35)	1.48)
	United States	2.49 (1.80-	1.02 (0.77-	1.52 (1.11-	1.02 (0.73-
		3.43)**	1.35)	2.07)**	1.43)
	Driving Exposure (Ref. category a few days a
	month)
	1 to 3 days a week	1.08 (0.89-	1.08 (0.86-	0.91 (0.71-	1.18 (0.95-
		1.33)	1.36)	1.16)	1.46)
	at least 4 days a week	1.77 (1.48-	1.78 (1.44-	1.51 (1.21-	1.57 (1.29-
		2.12)**	2.21)**	1.89)**	1.90)**
	Acceptability of Safe and Unsafe Behaviour (variable equal to 1 if respondent rated
	acceptability as 4 or 5 on 5-point scale; Ref. category 0 otherwise)
	Social acceptability to talk on a	1.79 (1.48-
	handheld phone while driving	2.16)**
	Social acceptability to read a text			1.92 (1.47-
	message/email or check social			2.50)**
	media while driving
	Personal acceptability to talk on a	3.62 (2.70-
	handheld phone while driving	4.86)**
	Personal acceptability to talk on a		2.49 (2.24-
	hands-free phone while driving		2.77)**
	Personal acceptability to read a text
	message/email or check social
	media while driving

All ESRA2 partners support and finance the national ESRA2 surveys in 32 countries.

ESRA is funded through the contributions of partner organisations, either from their own resources or from sponsoring. Part of the funding for the Vias institute is provided by the Belgian Federal Public Service Mobility and Transport.

List of Tables


Samia Guezane Lakoud

Rim Aissa

Regis Guillot

Martial Toffano

Louisa Aribi- Zouioueche

Professor Jean Claude Fiaud

Novel One-Pot Access to Diastereoisomeric Tertiary Phospholanes Oxides by Using Enantiomerically Pure Phospholane Oxides Under Catalyst-Free Conditions

For the first time, enantiopure 1-r-oxo-2-c,5-t-diphenylphospholane was introduced as nucleophile in the multicomponent condensation reaction. Diastereoisomers of 2,5-diphenyl-1-oxo-1-[alkylphenyl-1-(phenylamino) methyl] phospholane derivatives were synthesized by one-pot process from aromatic aldehydes, anilines and enantiopure1-r-oxo-2-c,5t-diphenylphospholane under green and eco-compatible conditions. The reaction proceeds under catalyst-free conditions at room temperature within very short time (3 min) in excellent yields (up to 95%). An X-ray crystal structure has been obtained for 2,5diphenyl-1-oxo-1-[phenyl (phenylamino) methyl] phospholane.

Introduction

P-chiral organophosphorus compounds have been widely used in organometallic chemistry, homogeneous catalysis agrochemical and pharmaceutical industries. [1] Phosphinylidene compounds are an important family of organophosphorus compounds, [2] which includes phosphinates, H-phosphonates, [3] H-phosphinates and secondary or tertiary phosphine oxides. [4], [5] The H-phosphonate forms were widely used as direct precursor in Kabachnik-Fields reaction for αaminophosphonates, [6] in Michaelis-Becker, Pudovic and Abramov reactions for amidophosphonates, phosphonic acids and hydroxyphosphonate derivatives in highly regio-, chemo-and stereoselective transformations. [7] H-phosphine oxides prove valuable ligands in transition metal-catalyzed reactions. [8] Tertiary phosphine oxides are an important compounds class in organophosphorus chemistry showing a strong contribution in the field of organometallic asymmetric catalysis. [START_REF]Phosphorus Ligands in Asymmetric Catalysis[END_REF] Considerable attention is continuously devoted to non racemic tertiary phosphine oxides, since their reduction is one of the most useful methods for the preparation of optically active tertiary phosphines. [10] Various approaches were also described to synthesize these precious targets: metal-free [11] or transition metal-catalyzed cross-coupling reactions, [12] Brønsted acid-catalyzed [13] synthesis and Grignard reagents. [14] Recently, secondary diphenylphosphine oxide was used in Kabachnik-Field reaction to form bis (phosphinoylmethyl) amine served as a precursor for an optically active bidentate P-ligand in the synthesis of a chiral platinum complex. [15] Phospholane oxides and their derivatives have been subjected to hydrophosphinylation, [16] and have emerged as effective pre-catalysts for an expanding new area of organocatalysts. [17] Furthermore, in a pioneering work, Fiaud and Co-worker demonstrated the potential of 1-oxo-2c,5t-diphenylphospholane A, as an intermediate for the preparation of 1-r,2-c,5-ttriphenylphospholane ligand. [18] Later this compound which presents a pseudo C2 axis was used as a building block to develop P-aryl-2-c,5-t-diphenylphospholane ligands family, hydrophosphinylation [19] or cross-coupling reaction. [20] Recently, Fiaud's acid or 1-oxo-1-hydroxy-2-c,5-t-diphenylphospholane, was introduced as an efficient chiral Brønsted acid catalyst for the synthesis of complex targets. [21] Due to the electronic density at the phosphorus atom and the equilibrium form, the cyclic 1-H-phosphine oxides are of exceptional interest as key intermediate to obtain original Pheterocyclic compounds. The monodentate phosphorus nature is likely to offer more efficient activity for metal or organocatalysis. [22] For 2,5-disubstitued phospholane compounds, we supposed that the relative electronic richness of phosphorus atom is an opportunity to promote original reactivity to obtain interesting structures. Moreover, the non- With this in mind, by choosing a judicious reaction type, it is possible to access to new phosphorus compounds. Especially, the access to P-N compounds is particularly interesting for the development of new ligands or organocatalysts. [23] Figure. 1 Equilibrium form of enantiopure secondary phospholane oxide Following our recent results concerning the enzyme-catalyzed synthesis of aminophosphonates and original bisaminophosphonates using free lipases and Candida antarctica B lipase immobilized on acrylic resin (CAL-B), [6a-b], [24] we propose herein to develop a multicomponent reaction for an access to an original chiral cyclic tertiary phosphine oxides via condensation reaction of aromatic aldehyde, aniline and cyclic enantiopure H-diphenyl phosphine oxide A as precursor. The reaction should proceed under free-catalysis, room temperature, short reaction times and environmentally benign reaction conditions. This study will be aimed at developing an efficient procedure for the preparation of the 2,5-diphenyl-1-oxo-1-[alkyl phenyl-1-(phenylamino) methyl] phospholane (R, R,R/S)-4a-j via modified Kabachnik-Fields reaction. These compounds would be obtained in two diastereomeric forms (Scheme 1).

Scheme 1 Preparation of tertiary phosphine oxides

Results and Discussion

Initially, we used H-diphenyl phosphine oxide (Ph2POH) C in the Kabachnik-Fields condensation reaction without catalyst. The reaction proceeded through the condensation reaction of benzaldehyde (101 mg, 1 mmol), aniline (184 mg, 1 mmol) and H-diphenyl phosphine oxide (256mg, 1 mmol) as model reaction, at room temperature in ethanol (1ml) (Table 1). The results show high reactivity of H-diphenyl phosphine oxide C, giving the amino tertiary phosphine oxide 3C after 10 minutes with 45% yield (Table 1, entry 1). Increasing the reaction time to 30 min led to 3C compound in excellent isolated yield (Table 1, entry 2). It clearly appears that H-diphenyl phosphine oxide displayed better reactivity than H-diethylphosphite D which previously tested under catalyst-free conditions to give α-aminophosphonate 3D (Table 1, entry 3 vs 2). Thereafter, and considering the reactivity of H-phosphine oxide C, we have investigated for the first time the use of enantiopure 1-r-oxo-2-c,5-t-diphenylphospholane A as a nucleophile in Kabachnik-Fields multicomponent reaction. The general procedure involved the condensation of aromatic aldehyde, aniline and enantiopure secondary phospholane oxide A at room temperature in the presence of ethanol in two cases; without catalyst or with the use of the free lipases and Candida antarctica B lipase immobilized on acrylicresin (CAL-B) (Table 1, entries 4 and 5) respectively.

2,5-diphenyl-1-oxo-1-[alkyl phenyl (phenylamino) methyl] phospholane 4a-j were obtained with high isolated yields in two diastereoisomers forms in a very short reaction time (3 min) (Table 2). Indeed, the diastereomeric ratio (d.r.) is obtained from 73/27 to 86/14 depending the nature of the substrates and the electronic effects. The observed diastereoselectivities suggest a partial control by the chiral secondary phospholane oxide during the nucleophilic addition step. We also observed a drop of diastereoselectivity in the case of substrate 1d and 1e. These results are probably due to the very high reactivity of the corresponding imine which reduces the enantioface recognition. All these compounds are novel in organophosphorus chemistry and the reactions were carried out through a very fast, atom economical and environmentally benign procedure. compounds 4a were separated by crystallization in ethanol, single crystal X-ray diffraction analysis of the major diastereoisomer compound releaved the configuration (2R, 5R, 1R) (CCDC 1922735; contain(s) the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif (Figure . 2).

Figure. 2 X-ray crystal structure of 4a

A possible mechanism for the formation of 2,5-diphenyl-1-oxo-1-[alkyl phenyl (phenylamino) methyl] phospholane 4 via Kabachnik-Fields condensation reaction with an equimolar quantity of starting materials (1/1/1 ratio) of aromatic aldehydes 1, anilines 2 and enantiopure secondary phospholane oxide A is shown in Scheme 2. Combining the view points developed by J. Zhang et al [25] for the synthesis of N-phosphoramino α-amino-alkyl phosphonates via diethyl phosphoramidate, ketones or aldehydes and 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphane through Mannich type reactions, and on the basis of our observations as described above, we proposed that the imine was formed at the first time between an aldehyde and aniline, following by the nucleophilic attack of the tautomerized trivalent form of the enantiopure secondary phospholane oxide to re-face and si-face of the imine giving the two diastereoisomers of 4.

Conclusions

As a conclusion, we report an original one-pot synthesis of chiral 2,5-diphenyl-1-oxo-1-[alkyl phenyl (phenylamino) methyl] phospholane using enantiopure 1-r-oxo-2-c,5-t-diphenylphospholane A in multicomponent coupling reaction with aromatic aldehydes and anilines. An X-ray crystal structure has been obtained for a diastereoisomer of 2,5diphenyl-1-oxo-1-[phenyl (phenylamino) methyl] phospholane 4a and the configuration assigned as (R, R, R). All compounds were obtained in high isolated yield (up > 95%) under greener more efficient novel approach: atom-economic process, catalystfree, very short reaction time in green solvent, at room temperature and with purification by simple crystallization. This is the first protocol of the use of enantiopure secondary phospholane oxide as the nucleophile in multicomponent reaction, providing anew access to valuable targets of the family of organophosphorus compounds.

[ a ]

 a Dr. S. Guezane Lakoud, R. Aissa, Prof. L. Aribi-Zouioueche. Ecocompatible Asymmetric Catalysis Laboratory.(LCAE) Badji Mokhtar Annaba-University. B.P 12, 23000 Annaba, Algeria. Email: Samia.guezanelakoud@univ-annaba.dz [b] Prof. R. Guilot, Dr. M. Toffano. Equipe de Catalyse Moléculaire-ICMMO Bât 420. Université Paris-Sud, Paris Saclay, 91405 Orsay cedex, France. Electronic Supplementary Information (ESI) available: [Further experimental information and characterization of products]. See DOI: 10.1039/x0xx00000x. stereogenic property of the phosphorus atom should avoid all problem of stereochemical integrity. The origin of chirality on the carbon frame as well as the five-membered cyclic chain would provide good asymmetric induction (Figure. 1).

Scheme 2

 2 Scheme 2 Proposed reaction mechanism for the synthesis of 4

Table . 1

 . Different phosphorus oxides tested as nucleophile in multicomponent Kabachnik-Fields reaction.

	Entry	Phosphorus oxide	Catalyst	Time/min	Yield(%) a
					/ Product
	1	H-diphenyl phosphine	--	10	45/3C
		oxide C
	2	H-diphenyl phosphine	--	30	80/3C
		oxide C
	3	H-diethyl phosphite D	--	60	---/3D
	4	Cycle H-phospholane	--	3	96 /4a
		oxide (R, R)-A
	5	Cycle H-phospholane	CAL-B	3	96/4a
		oxide (R, R)-A

a Isolated yield after crystallization in hexane.

P and 1 H NMR experiments were used for diastereomer quantification. The 31 P NMR spectra exhibited two peaks for the two diastereoisomers at around 62 and 61 ppm. From the 1 H NMR spectra, the proton of the three stereogenic carbons *CHP of two diastereoisomers appears clearly as a multiplet towards 4 ppm due to the coupling with P atoms, and nitrogen protons NH of two diastereoisomers are very clearly exhibited as doublets around 5 ppm. The two diastereoisomeric

Acknowledgements

The Algerian Ministry of Higher Education and Scientific Research (MESRS, FNR 2000) is gratefully acknowledged for financial support of this work.

Keywords: Cyclic enantiopure, H-diphenyl phosphine oxide, Kabachnik-Fields reaction, Multicomponent reactions, Secondary phosphine oxides, Tertiary phosphine oxides.

Supporting Information Summary

Supporting information file includes the general experimental procedure, compound characterization data and the 1 H, 13 C and 31 P NMR spectra and HRMS of all the compounds.