Synlett 2004(13): 2369-2373  
DOI: 10.1055/s-2004-832840
LETTER
© Georg Thieme Verlag Stuttgart · New York

Oxidation of Secondary Alcohols with Phenyltrimethylammonium Tribromide in the Presence of a Catalytic Amount of Antimony(III) Bromide or Copper(II) Bromide

Shinsei Sayama*, Tetsuo Onami
Department of Chemistry, Fukushima Medical University, Hikariga-oka, Fukushima 960-1295, Japan
Fax: +81(24)5471369; e-Mail: ssayama@fmu.ac.jp;
Further Information

Publication History

Received 22 July 2004
Publication Date:
28 September 2004 (online)

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Abstract

The oxidation of alcohols was carried out with phenyl­trimethylammonium tribromide in the presence of a catalytic amount of SbBr3 or CuBr2. 1,2-Diols, such as hydrobenzoin, were converted into 1,2-diketones or α-ketols without oxidative cleavage of the glycol C-C bond at room temperature. A variety of secondary alcohols were also oxidized to the corresponding carbonyl compounds in a chemoselective manner.