Financial support from the NSF (CHE 0808825) is gratefully acknowledged. We also thank the JSPS for Fellowships (R.K. and Y.I.) and Dr. J. C. Daran for his help with the crystallographic part of this manuscript.
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Communication
Isolation of Bicyclopropenylidenes: Derivatives of the Smallest Member of the Fulvalene Family†
Article first published online: 12 DEC 2008
DOI: 10.1002/anie.200804372
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Kinjo, R., Ishida, Y., Donnadieu, B. and Bertrand, G. (2009), Isolation of Bicyclopropenylidenes: Derivatives of the Smallest Member of the Fulvalene Family. Angewandte Chemie International Edition, 48: 517–520. doi: 10.1002/anie.200804372
- †
Publication History
- Issue published online: 29 DEC 2008
- Article first published online: 12 DEC 2008
- Manuscript Received: 4 SEP 2008
Funded by
- NSF. Grant Number: CHE 0808825
Keywords:
- carbenes;
- cyclopropenylidenes;
- fulvalenes;
- hydration;
- strained molecules
Graphical Abstract
Small and stable: A triafulvalene derivative is indefinitely stable at room temperature both in solution and in the solid state under inert atmosphere. The triafulvalene is synthesized by the magnesium-catalyzed coupling of two bis(chlorocyclopropenyl) derivatives. The two unsaturated three-membered rings are linked together by a carbon–carbon double bond (1.303 Å, see structure), which is so reactive that spontaneous addition of water occurs at room temperature.