The Reaction of Thiols and α,ω-Dithiols With Triphenylphosphine and Diisopropyl Azodicarboxylate

Abstract

α,ω-Dithiols in the presence of triphenylphosphine and diisopropyl azodicarboxylate are converted into a mixture of monomeric and polymeric disulfides. The product distribution is dependent on the alkyl chain length and the reaction conditions. In contrast to normal Mitsunobu reactions, disulfide bond formation is achieved with regeneration of triphenylphosphine. The mechanism of this reaction is discussed.