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Synfacts 2006(4): 0336-0336  
DOI: 10.1055/s-2006-932060
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

An Unusually Long-Lived Triplet Carbene

Contributor(s): Timothy M. Swager, Trisha L. Andrew
T. Itoh, Y. Nakata, K. Hirai*, H. Tomioka*
Mie University and Aichi Institute of Technology, Japan
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

Compound 1, a triplet carbene that survives for almost one day in a 2-methyltetrahydrofuran solution at room temperature, is synthesized and characterized. The long lifetime of 1 is ascribed to the presence of two proximate trifluoromethyl groups, which, due to their spatial distribution, kinetically protect the carbene from undergoing degradation reactions.