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Thiolysis of Alkyl‐ and Aryl‐1,2‐epoxides in Water Catalyzed by InCl 3
Author(s) -
Fringuelli Francesco,
Pizzo Ferdinando,
Tortoioli Simone,
Vaccaro Luigi
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200206)344:3/4<379::aid-adsc379>3.0.co;2-4
Subject(s) - thiolysis , chemistry , thiophenol , nucleophile , catalysis , alkyl , aryl , regioselectivity , organic chemistry , medicinal chemistry , antioxidant , polyphenol , proanthocyanidin
The pH dependence of thiolysis of 1,2‐epoxides with thiophenol in water and the influence of a Lewis acid catalyst is investigated. InCl 3 showed a very high efficiency in catalyzing this process at pH 4.0. The regioselectivity of the nucleophilic attack is markedly influenced going from pH 9.0 to pH 4.0. A one‐pot procedure running solely in water to prepare trans ‐2‐(phenylsulphinyl)cyclohexan‐1‐ol is reported starting from epoxycyclohexane, via thiolysis reaction and oxidation with t ‐butyl hydroperoxide.