Novel Rearrangements of 2,3-Dimercapto-1-propanol Derivatives: Formation of Dialkyl Sulfide, Dialkyl Disulfide, and 1,2,3-Tris(alkylthio)propane

Chi Wi Ong; Yi Meen Chou; Junn Nan Wang

doi:10.1021/jo960784s

Novel Rearrangements of 2,3-Dimercapto-1-propanol Derivatives: Formation of Dialkyl Sulfide, Dialkyl Disulfide, and 1,2,3-Tris(alkylthio)propane

J Org Chem. 1996 Nov 15;61(23):8244-8247. doi: 10.1021/jo960784s.

Authors

Chi Wi Ong¹, Yi Meen Chou, Junn Nan Wang

Affiliation

¹ Department of Chemistry, National Sun Yat Sen University, Kaoshiung, Taiwan 804.

PMID: 11667811
DOI: 10.1021/jo960784s

Abstract

The base alkylation of 2,3-dimercapto-1-propanol with alkyl halides leads in good yield to 2,3-bis(alkylthio)-1-propanol and dialkyl sulfide. The reaction of 2,3-bis(alkylthio)-1-propanol with catalytic concentrated sulfuric acid proceeds with rearrangement to give 1,2,3-tris(alkylthio)propane and dialkyl disulfide. The rearrangement reaction takes place through a common intermediate thiaranium intermediate 8.