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1. Thermal Reactions of β-Hydroxysulfides Bearing Benzothiazole: Sulfenic Acid Trapping via a Spiro Intermediate.

Author

Yamada, Nobuhiko, Koyasu, Takanori, Sonami, Mayumi, Aoi, Michiko, Tashiro, Shintaro, Sheikh, Chanmiya, Ishida, Yusuke, Kawashima, Wataru, Yoshimura, Toshiaki, and Morita, Hiroyuki

Subjects
BENZENE, SULFOXIDES, SULFENIC acids, THERMAL analysis, THIOLS
Abstract

Benzothiazolyl 2-hydroxyethyl sulfoxide (1a) was found to afford bis[2-(2-oxobenzotiazolyl)-ethyl] disulfide (2a) in the presence of DBU at rt. 2a was formed by the condensation of corresponding sulfenic acid intermediate. Thermolyses of 1a in the presence of ethyl propiolate at 60-140°C were carried out to succeed to trap sulfenic acid 6a as an intermediate. Trapping of 2-benzothiazolyloxyenthanesulfenic acid (6a) revealed that the thermal reaction proceeded via a five-membered spiro intermediate 5a. [ABSTRACT FROM AUTHOR]

Published
2010
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