Jean-Luc Mieusset, A. Schrems, M. Abraham
Jan 24, 2009
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Influential Citations
7
Citations
Journal
Tetrahedron
Abstract
Abstract The reactivity of stabilized-nucleophilic carbene tricyclo[6.2.1.0 2,7 ]undec-9-en-11-ylidene ( 9 ) toward C–H insertions has been investigated. It is shown that 9 can only insert into acidic C–H bonds, for example, in malononitrile. In this case, evidence for a stepwise process has been obtained. Protonation of the carbene leads to an ion pair composed of a carbocation and a carbanion, which subsequently reacts and gives rise to the formal insertion product anti 10 .