62291-78-5Relevant academic research and scientific papers
Thiolysis of Alkyl- and Aryl-1,2-epoxides in Water Catalyzed by InCl3
Fringuelli, Francesco,Pizzo, Ferdinando,Tortoioli, Simone,Vaccaro, Luigi
, p. 379 - 384 (2002)
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.
ZnCl2 as an Efficient Catalyst in the Thiolysis of 1,2-Epoxides by Thiophenol in Aqueous Medium
Amantini, David,Fringuelli, Francesco,Pizzo, Ferdinando,Tortoioli, Simone,Vaccaro, Luigi
, p. 2292 - 2296 (2007/10/03)
ZnCl2 (5 mol%) is an efficient catalyst for the thiolysis of 1,2-epoxides by thiophenol in water at pH 4.0. A variety of β-hydroxy phenylsulfides were obtained in short reaction times and excellent yields. Starting from cyclohexene oxide (1), two one-pot multi-step procedures in sole water (thiolysis/oxidation with H2O2) have been realized, for the chemoselective synthesis of the corresponding β-hydroxysulfoxides 19 or for the related β-hydroxysulfone 20.
