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

Author:

Buron Christophe1,Gornitzka Heinz1,Romanenko Vadim1,Bertrand Guy1

Affiliation:

1. Laboratoire d'Hétérochimie Fondamentale et Appliquée, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse cedex 04, France.

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.

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

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4. M. Jones and R. A. Moss Eds. Carbenes vol. II (Wiley New York 1975).

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