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Résumé :
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Oils and fats are an important source of renewable raw materials, and the availability of functionalized fatty acids such as epoxy ring containing fatty acids gives us a convenient source of starting materials for the synthesis of various biodegradable derivatives. Methyl esters of the epoxidized oleic acid [methyl 9,10-epoxy octadecanoate (1)] on the catalytic epoxy ring opening reaction with various aliphatic [butyl (2), octyl (3)], cyclic [pyrrolidine (4), piperidine (5), morpholine (6)], and aromatic [p-chloroaniline (7), p-anisidine (8), benzyl amine (9), aniline (10)] amines resulted in the formation of the respective β-amino alcohols [methyl 9-(butylamino)-10-hydroxyoctadecanoate (11a)/methyl 10-(butylamino)-9-hydroxyoctadecanoate (11b), methyl 10-hydroxy-9-(octylamino)octadecanoate (12a)/methyl 9-hydroxy-10-(octylamino)octadecanoate (12b), methyl 10-hydroxy-9-(pyrrolidin-1-yl)octadecanoate (13a)/methyl 9-hydroxy-10-(pyrrolidin-1-yl)octadecanoate (13b), methyl 10-hydroxy-9-(piperidin-1-yl)octadecanoate (14a)/methyl 9-hydroxy-10-(piperidin-1-yl)octadecanoate (14b), methyl 10-hydroxy-9-morpholinooctadecanoate (15a)/methyl 9-hydroxy-10-morpholinooctadecanoate (15b), methyl 9-(4-chlorophenylamino)-10-hydroxyoctadecanoate (16a)/methyl 10-(4-chlorophenylamino)-9-hydroxyoctadecanoate (16b), methyl 10-hydroxy-9-(4-methoxyphenylamino)octadecanoate (17a)/methyl 9-hydroxy-10-(4-methoxyphenylamino)octadecanoate (17b), methyl 9-(benzylamino)-10-hydroxyoctadecanoate (18a)/methyl 10-(benzylamino)-9-hydroxyoctadecanoate (18b), methyl 10-hydroxy-9-(phenylamino)octadecanoate (19a)/methyl 9-hydroxy-10-(phenylamino)octadecanoate (19b)] as isomeric mixtures. Zinc(II) perchlorate hexahydrate was used as a Lewis acid catalyst to achieve these transformations under solvent-free conditions.
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