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Science 8 June 2001:
Vol. 292. no. 5523, pp. 1901 - 1903
DOI: 10.1126/science.292.5523.1901
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Reports

(Amino)(Aryl)Carbenes: Stable Singlet Carbenes Featuring a Spectator Substituent

Stéphane Solé,1 Heinz Gornitzka,1 Wolfgang W. Schoeller,2 Didier Bourissou,1 Guy Bertrand1*

Several (amino)(aryl)carbenes have been shown to be stable at room temperature in solution and in the solid state. Electroneutrality of the carbene center is ensured by the amino group, which has both pi -donor and sigma -acceptor electronic character. The aryl group remains a spectator substituent, as shown by single-crystal x-ray analysis and by its chemical behavior. Because only one electron-active substituent is needed, numerous stable carbenes will become accessible, which will open the way for new synthetic developments and applications in various fields.

1 Laboratoire d'Hétérochimie Fondamentale et Appliquée, Université Paul Sabatier, 118 route de Narbonne, F-31062 Toulouse Cédex 04, France.
2 Fakultät für Chemie der Universität, Postfach 10 01 31, D-33615 Bielefeld, Germany.
*   To whom correspondence should be addressed. E-mail: gbertran{at}ramses.ups-tlse.fr

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Science. ISSN 0036-8075 (print), 1095-9203 (online)