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Synfacts 2006(8): 0837-0837  
DOI: 10.1055/s-2006-942004
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

A New Dichlorocarbenoid Equivalent for Cyclopropanation and Olefination

Contributor(s): Paul Knochel, Andrei Gavryushin
C.-T. Chien, C.-C. Tsai, C.-H. Tsai, T.-Y. Chang, P.-K. Tsai, Y.-C. Wang, T.-H. Yan*
National Chung-Hsing University, Taiwan, P. R. of China
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

This is an easy and elegant method of the cyclopropanation of alkenes leading to 1,1-di­chlorocyclopropanes as well as the dichloromethylenation of a broad spectrum of carbonyl compounds. The method to generate dichlorocarbene is extremely simple and all the reagents are readily available. Even a catalytic amount of TiCl4 is sufficient for the cyclopropanation process. Remarkably, ketones can be readily transformed by this method into dichloroolefins, which are often difficult to prepare otherwise.