Highly Efficient C-C Bond-Forming Reactions of an α-Cyanoketene Dithioacetal with Aldehydes and Ketones

Qian Zhang; Yu Liu; Mang Wang; Qun Liu; Jianglei Hu; Yanbing Yin

doi:10.1055/s-2006-942530

PAPER

Highly Efficient C-C Bond-Forming Reactions of an α-Cyanoketene Dithioacetal with Aldehydes and Ketones

Qian Zhang*, Yu Liu, Mang Wang, Qun Liu*, Jianglei Hu, Yanbing Yin
Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. of China
e-Mail: zhangq651@nenu.edu.cn;

Abstract

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Abstract

In the presence of titanium(IV) chloride, the C-C bond-forming reaction of the α-cyanoketene cyclic dithioacetal 1,3-dithiolan-2-ylideneacetonitrile with various aldehydes and ketones afforded multifunctional pentanedinitriles, 3-substituted- or 3,3-disubstituted 2,4-di-1,3-dithiolan-2-ylidenepentanedinitriles, respectively, in good to excellent yields under very mild conditions. A possible mechanism involving consecutive C-C bond formation was proposed.

Key words

carbon-carbon bond-forming reaction - α-cyanoketene cyclic dithioacetal - aldehydes - ketones - 2,4-di-1,3-dithiolan-2-ylidenepentanedinitriles

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