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Synthesis 2009(14): 2371-2378  
DOI: 10.1055/s-0029-1216861
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Sulfanyl-Substituted [3]Cumulenes and Buta-1,3-dienes from a Tetrakis(pyridinium)-Substituted Butadiene

Andreas Schmidt*a, Alireza Rahimia, Mimoza Gjikajb
a Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstraße 6, 38678 Clausthal-Zellerfeld, Germany
Fax: +49(5323)723861; e-Mail: schmidt@ioc.tu-clausthal.de;
b Institute of Inorganic Chemistry, Clausthal University of Technology, Paul-Ernst-Straße 4, 38678 Clausthal-Zellerfeld, Germany
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Publication History

Received 22 January 2009
Publication Date:
29 May 2009 (online)

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Abstract

Treatment of perchlorobuta-1,3-diene with 4-(N,N-di­methylamino)pyridine resulted in the formation of 1,1′,1′′,1′′′-(2,3-dichlorobuta-1,3-diene-1,1,4,4-tetrayl)tetrakis[4-(dimethylami­no)pyridinium] tetrachloride (structure confirmed by X-ray analysis), which was converted into persulfurated butatrienes ([3]cumulenes), pentakis(sulfanyl)-substituted buta-1,3-dienes, or tetrakis(sulfanyl)-substituted 2,3-dichlorobuta-1,3-dienes by reactions with thiolates or a sulfinate. The outcome of the reaction depends on the reaction conditions and the substitution pattern of the starting sulfur nucleophiles.

Key words

dienes and trienes - sulfides - pyridines - perchlorinated compounds - persulfurated compounds