An isolable cyclopropenylidene derivative

ORGN 862

Vincent Lavallo, vincentlavallo@hotmail.com, UCR/CNRS Joint Research Laboratory, University of California Riverside, Department of Chemistry, Riverside, CA 92507 and Guy Bertrand, gbertran@mail.ucr.edu, UCR/CNRS Joint Research Chemistry Laboratory, UC Riverside, Riverside, CA 92521-0403.
The singlet carbene cyclopropenylidene (C3H2) has been detected in the interstellar medium, but been presumed too unstable to isolate in the laboratory. However, by attaching electron donating amino groups to the three membered ring skeleton, we have prepared a cyclopropenylidene derivative that is isolable in the laboratory at room temperature. This is the first isolated carbene that is not stabilized by the presence of pi-donor heteroatoms directly linked to the electron-deficient carbon center. As revealed by x-ray crystallography the presence of amino groups does not significantly perturb the geometric parameters of the triangular skeleton, relative to those of the calculated parent cyclopropenylidene. Our first results concerning the use of stable cyclopropenylidenes as ligands for transition metal catalysts and as organic catalysts on their own right will be discussed.