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Synthesis 2010(15): 2616-2620  
DOI: 10.1055/s-0029-1218820
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

2-(Trimethylsilyl)-1,3-dithiane 1-Oxide as a Convenient Reagent for the Transformation of Aldehydes and Ketones into Homologous Carboxylic Acids

Karsten Krohn*, Stephan Cludius-Brandt
Department Chemie, Universität Paderborn, Warburger Str. 100, 33098 Paderborn, Germany
Fax: +49(5251)603245; e-Mail: k.krohn@uni-paderborn.de;
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Publication History

Received 14 February 2010
Publication Date:
17 June 2010 (online)

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Abstract

Aldehydes and ketones were converted into the corresponding homologous carboxylic acids in two steps by treatment with 2-(trimethylsilyl)-1,3-dithiane 1-oxide. A modified Peterson olefination of the carbonyl compounds gave ketene thioacetal sulf­oxides that were readily cleaved in acidic acetonitrile to give the required carboxylic acids.

Key words

aldehydes - ketones - carboxylic acids - homologation

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