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Synthesis 2003(6): 0820-0822
DOI: 10.1055/s-2003-38691
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Base-Induced Reactions of 3-Phenylsulfonylpropyl- and 3-Cyanopropyl­trimethylammonium Chlorides with Aldehydes: New Synthesis of Substituted Butadienes

Mieczysław Mąkosza*, Marek Judka
Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, 01-224 Warszawa 42, POB 58, Poland
Fax: +48(22)6326681; e-Mail: icho-s@icho.edu.pl;
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Publication History

Received 23 January 2003
Publication Date:
16 April 2003 (online)

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Abstract

3-Phenylsulfonylpropyltrimethylammonium chloride and 3-cyanopropyltrimethylammonium chloride react with aromatic aldehydes in the presence of excess of potassium tert-butoxide and methyl iodide to give 1,2-disubstituted 1,3-butadienes.

Key words

aldehydes - butadienes - carbanions - Hofmann elimination - quaternary ammonium