Oxidations with lead tetraacetate. V. Oxidations of 1,3-benzoxathioles

Abstract

2,2-Disubstituted 1,3-benzoxathioles are easily oxidized by lead tetraacetate to a complex mixture of products. Acetoxylation takes place on the first carbon atom of the 2-alkyl or -cycloalkyl sub- stituent giving acetoxy derivatives. The hetero ring is also opened yielding ketones, acetoxyketones, a disulfide and polymeric materials. Oxidation at the sulfur atom appears to be a minor reaction and no products oxidized in the benzene ring are found.