Synthesis of new heterocycles by oxidation of functionalized cyclic derivatives of bis(2-chlorovinyl) sulfide and selenide

Abstract

Oxidation of 4-substituted 2,6-bis[(E)-chloromethylidene]thiomorpholine with hydrogen peroxide in a mixture of chloroform with acetic acid afforded the corresponding 4-R-2,6-bis[(E)-chloromethylidene]-thiomorpholine 1-oxide. The results of oxidation of bis[(E)-chloromethylidene]-1,4-dichalcogenanes under analogous conditions depended on the chalcogen nature and its position in the ring. The reaction of 2,6-bis[(E)-chloromethylidene]-1,4-dithiane gave 2,6-bis[(E)-chloromethylidene]-1,4-dithiane-1,1,4,4-tetraone, whereas 3,5-bis[(E)-chloromethylidene]-1,4-thiaselenane-1,1-dione was unexpectedly obtained from 3,5-bis[(E)-chloromethylidene]-1,4-thiaselenane. 2,6-Bis[(E)-chloromethylidene]-1,4-thiaselenane and 2,6-bis[(E)-chloromethylidene]-1,4-diselenane decomposed under the oxidation conditions.