Bulletin of the Chemical Society of Japan

The Hydroboration of 1-Alkylthio-l-alkynes, and Its Application to the Syntheses of S-Alkyl Alkanethioates and (Z)-1-Alkylthio-1-alkenes

M Hoshi, Y Masuda, A Arase

Index: Hoshi; Masuda; Arase Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 2 p. 447 - 452

Full Text: HTML

Citation Number: 21

Abstract

Hydroboration of 1-alkylthio-1-alkynes with dicyclohexylborane or bis (1, 2-dimethylpropyl) borane proceeded smoothly, adding most of the dialkylboryl group to the α-position of the triple bond. The resulting alkenylboranes afforded either S-alkyl alkanethioates on a controlled oxidation with alkaline hydrogen peroxide in the presence of N, N, N′, N′- etramethylethylenediamine or (Z)-1-alkylthio-1-alkenes on a basic protonolysis, ...