Novel Rearrangements of 2,3-Dimercapto-1-propanol Derivatives: Formation of Dialkyl Sulfide, Dialkyl Disulfide, and 1,2,3-Tris(alkylthio)propane.
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.
Ong
Chi Wi
CW
Department of Chemistry, National Sun Yat Sen University, Kaoshiung, Taiwan 804.
Chou
Yi Meen
YM
Wang
Junn Nan
JN