ZnCl2 as an Efficient Catalyst in the Thiolysis of 1,2-Epoxides by Thiophenol in Aqueous Medium

David Amantini; Francesco Fringuelli; Ferdinando Pizzo; Simone Tortoioli; Luigi Vaccaro

doi:10.1055/s-2003-42107

LETTER

ZnCl₂ as an Efficient Catalyst in the Thiolysis of 1,2-Epoxides by Thiophenol in Aqueous Medium

David Amantini, Francesco Fringuelli, Ferdinando Pizzo*, Simone Tortoioli, Luigi Vaccaro*
Dipartimento di Chimica, Università di Perugia, Via Elce di Sotto, 8 06123 Perugia, Italy
Fax: +39(075)5855560; e-Mail: pizzo@unipg.it; luigi@unipg.it ;

Abstract

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Abstract

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.

Key words

aqueous medium - thiolysis - 1,2-epoxides - ZnCl₂ - catalysis

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Referenzen

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