The First Synthesis of Aliphatic Sulfines from Thiono-esters

Article abstract of DOI:10.1016/0040-4039(91)80120-U

Reaction of various thiono-esters with one equivalent of meta-chloroperoxybenzoic acid at 0 deg C in dichloromethane furnishes the corresponding sulfines, evidenced for the first time.These thiocarbonyl oxides are rather unstable at room temperature and give carboxylic esters, with loss of sulfur.The overall sequence provides an easy and quantitative C=S -> C=O transformation.