Report

Stable Versions of Transient Push-Pull Carbenes: Extending Lifetimes from Nanoseconds to Weeks

Science  05 May 2000:
Vol. 288, Issue 5467, pp. 834-836
DOI: 10.1126/science.288.5467.834

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Abstract

A (phosphanyl)(trifluoromethyl)carbene is shown to be stable for weeks in solution at temperatures up to −30°C. Its chemical behavior exactly matches that of its transient congeners, even to the extent that subtle effects, such as the recently discovered weak π interaction with aromatics, are observed. The influence of substituents on the structure of push-pull carbenes is demonstrated by a single-crystal x-ray diffraction study of a (phosphanyl)[2,6-bis(trifluoromethyl)phenyl]carbene. The lifetime of these molecules makes them accessible to a wider range of standard techniques, allowing their chemical and physical behaviors to be studied in more detail than was previously possible.

  • * To whom correspondence should be addressed. E-mail: gbertran{at}ramses.ups-tlse.fr

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