Oxidations with lead tetraacetate. IV. Oxidations of 1,3-benzodithioles

Abstract

Oxidations of 2,2-dialkyl and spiro[1,3-benzodithiole-2,1'-cycloalkanes] with lead tetraacetate gave mainly sulfoxides and disulfoxides. The stereochemistry of these products was elucidated by n.m.r. spectroscopy. Oxidation of 2-methyl-2-aryl derivatives gave sulfoxides as minor products; here the main products were derived from attack on the methyl group forming acetoxy, diacetoxy, formyl and carboxylic acid derivatives and ring cleavage products. 2,2-Diaryl derivatives also formed small amounts of sulfoxides but ring cleavage products were predominant. Monosubstituted benzodithioles were very reactive and produced a variety of oxidation products, mostly unidentified.