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Cyclopropenation of Alkylidene Carbenes Derived from α-Silyl Ketones

Jingwei Li, Chunrui Sun and Daesung Lee*

*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, Email:

J. Li, C. Sun, D. Lee, J. Am. Chem. Soc., 2010, 132, 6640-6641.

DOI: 10.1021/ja101998w

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A new cyclopropenation reaction, which involves Cα-Si bond insertion of alkylidene carbenes derived from α-silyl ketones, features excellent selectivity for insertion into Cα-Si bonds rather than insertion into Cγ-H bonds or addition to γ,δ-double or -triple bonds. The selectivity trend clearly indicates that the α-oxygen in the tether significantly promotes Cγ-H insertion.

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Key Words

cyclopropenes, vinylsilanes

ID: J48-Y2010-1360