Tetrahedron

Aminolysis of sulfinamoyl-esters,-sulfonamides and-sulfones. Thiooxamate and thiourea formation via a sulfine intermediate. Thiophilic or carbophilic reaction?

…, K Raouf-Benchekroun, A De Blic, L Cazaux, P Tisnès…

Index: Baltas; Raouf-Benchekroun; De Blic; Cazaux; Tisnes; Gorrichon; Hussein; Barthelat Tetrahedron, 1996 , vol. 52, # 47 p. 14865 - 14876

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Citation Number: 11

Abstract

The aminolysis process of sulfinamoyl derivatives was investigated with sulfinamoyl esters. An intermediate sulfine was unambiguously evidenced by formation of a Diels-Alder type adduct. The aminolysis leads to final thiooxamate products. A carbophilic addition was suggested for the reaction with secondary amines. With sulfinamoyl,-sulfones and- sulfonamides, a thiourea is formed resulting from a double aminolysis.