Table of Contents
Organic Chemistry International
Volume 2014, Article ID 358932, 6 pages
http://dx.doi.org/10.1155/2014/358932
Research Article

In Quest of “Stereoselective Switch” for On-Water Hydrothiolation of Terminal Alkynes Using Different Additives and Green Synthesis of Vicinal Dithioethers

Department of Chemistry, North Bengal University, Darjeeling 734 013, India

Received 30 October 2013; Accepted 18 December 2013; Published 13 February 2014

Academic Editor: Ralph Nicholas Salvatore

Copyright © 2014 Basudeb Basu et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

On-water hydrothiolation reaction between terminal alkyne and thiol has been probed in the presence of various additives. Aromatic alkynes yield corresponding 1-alkenyl sulfides, whereas aliphatic alkynes undergo double-addition yielding vicinal disulfides in good to excellent yields. Formation of 1-alkenyl sulfides proceeds with a high degree of regioselectivity (via anti-Markovnikov addition), and switching the stereoselectivity between E/Z isomers has been noticeably realized in the presence of different additives/promoters.