Tetrahedron

Addition nucleophile des anions d'esters α-cyanoacetiques sur les cations succinimidosulfonium: Fragmentation ionique ou radicalaire des′ σ-sulfuranes …

…, MA LeMoing-Orliac, S Khamsitthideth, A Foucaud

Index: Morel, G.; Lemoing-Orliac, M. A.; Khamsitthideth, S.; Foucaud, A. Tetrahedron, 1982 , vol. 38, # 4 p. 527 - 537

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Citation Number: 3

Abstract

Reactions of substituted cyanoacetate anions 4 with S, S-dialayklsuccinimidosulfonium 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 σ-sulfurane intermediates. Homolytic cleavage of these ...