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Synthesis 2006(18): 3009-3014
DOI: 10.1055/s-2006-942530
DOI: 10.1055/s-2006-942530
PAPER
© Georg Thieme Verlag Stuttgart · New York
Highly Efficient C-C Bond-Forming Reactions of an α-Cyanoketene Dithioacetal with Aldehydes and Ketones
Further Information
Received
8 May 2006
Publication Date:
02 August 2006 (online)
Publication History
Publication Date:
02 August 2006 (online)
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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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