Preparation of sulfines by chlorination of dithiocarboxylic esters

Abstract

Abstract A new and simple method for the conversion of the highly substituted arenedithiocarboxylates 1a‐d into the corresponding sulfines (thione oxides) 3a‐d by chlorination and subsequent hydrolysis is described. The geometrical isomers of these sulfines are formed in the ratio 1:1. An excessive chlorination of the unhindered dithioesters 1e‐i results in (α,α‐dichloroaryl) sulfenyl chlorides 4, which can be converted into either thiobenzoyl chlorides by treatment with triphenylphosphine, or chlorosulfines by reaction with water and pyridine. Also an improved preparation of dichlorosulfine is described.