Isolation of Bicyclopropenylidenes: Derivatives of the Smallest Member of the Fulvalene Family†
Rei Kinjo Dr.
UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/
Search for more papers by this authorYutaka Ishida Dr.
UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/
Search for more papers by this authorBruno Donnadieu
UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/
Search for more papers by this authorGuy Bertrand Prof.
UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/
Search for more papers by this authorRei Kinjo Dr.
UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/
Search for more papers by this authorYutaka Ishida Dr.
UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/
Search for more papers by this authorBruno Donnadieu
UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/
Search for more papers by this authorGuy Bertrand Prof.
UCR–CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/
Search for more papers by this authorFinancial 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.
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.
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