ADDITION NUCLEOPHILE DES ANIONS D'ESTERS α-CYANOACETIQUES SUR LES CATIONS SUCCINIMIDOSULFONIUM. FRAGMENTATION IONIQUE OU RADICALAIRE DES ?-SULFURANES INTERMEDIAIRES

Article abstract of DOI:10.1016/0040-4020(82)80097-5

Reactions of substituted cyanoacetate anions 4 with S,S-dialkylsuccinimidosulfonium salts resulted generally in the formation of N-alkylthiomethylketenimines and α-alkylthiomethylesters.Coupling products were also obtained with anion 4d and only observed in the case of methyl phenylcyanoacetate anion 4b.The results were interpreted by the formation of instable ?-sulfurane intermediates.Homolytic cleavage of these intermediates gave radical pairs, then the coupling products.Heterolytic cleavage gave new sulfonium salts which rearranged via sulfonium ylides.