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Start Over Author "Fringuelli, Francesco" Journal advanced synthesis & catalysis
3 results on '"Fringuelli, Francesco"'

3. Thiolysis of Alkyl- and Aryl-1,2-epoxides in Water Catalyzed by InCl<INF>3</INF>

Author

Fringuelli, Francesco, Pizzo, Ferdinando, Tortoioli, Simone, and Vaccaro, Luigi

Abstract

The pH dependence of thiolysis of 1,2-epoxides with thiophenol in water and the influence of a Lewis acid catalyst is investigated. InCl3 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.

Published
2002
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