Chemical oxidation studies of beta-hydroxy-sulfides with tris(4-bromophenyl)aminium hexachloroantimonate: Diastereoselective sulfoxide obtaining and pinacol-type rearrangement | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

7953080

Reference Type

Journal Article

Title

Chemical oxidation studies of beta-hydroxy-sulfides with tris(4-bromophenyl)aminium hexachloroantimonate: Diastereoselective sulfoxide obtaining and pinacol-type rearrangement

Author(s)

Donnici, CL; Guimaraes, S; de Melo, AC

Year

2003

Is Peer Reviewed?

Journal

Synthetic Communications
ISSN: 0039-7911

Volume

Issue

Page Numbers

1489-1497

Language

English

DOI

10.1081/SCC-120018767

Web of Science Id

WOS:000182804500009

Abstract

The chemical oxidation of some β-hydroxy-sulfides in the presence of tris(4-bromo-phenyl)aminium hexachloroantimonate (TBPA) is reported. The oxidation of 2-ethylsulfanyl-cyclohexan-1-ol (cis- and trans-) resulted the corresponding sulfoxides with good diastereoselectivity (d.e. ≊50%) and for 2-methyl-2-ethylsulfanyl-cyclohexan-1-ol and 2-ethylsulfanyl-1,2-diphenyl-ethanol, the corresponding nonsulfanylated ketones (61-75%) and ethyl ethanethiolsulfonate (51-65%) were obtained via oxidative cleavage and pinacol-type rearrangement.