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Note | Regular issue | Vol 78, No. 8, 2009, pp.2077-2083
Published online, 6th April, 2009
DOI: 10.3987/COM-09-11687
One-Pot Synthesis of 4-Substituted Isothiochroman-1-thiones from α-Substituted 2-Bromostyrenes and Carbon Disulfide

Shuhei Fukamachi, Miyuki Tanmatsu, Hisatoshi Konishi, and Kazuhiro Kobayashi*

*Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

A facile method for the preparation of isothiochroman-1-thiones has been developed. Thus, treatment of a-substituted 2-lithiostyrenes, generated in situ from bromine-lithium exchange between the respective 2-bromostyrenes and butyllithium, with carbon disulfide, followed by workup with saturated aqueous ammonium chloride, affords 4-substituted isothiochroman-1-thiones in reasonable yields.