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

Article abstract of DOI:10.1016/0040-4020(96)00919-2

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.