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A Computational Investigation of the Reactions of Methylene, Chlorocarbene, and Dichlorocarbene with Cyclopropane

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journal contribution
posted on 23.01.2004, 00:00 by Fatma Sevin, Michael L. McKee, Philip B. Shevlin
The reactions of CH2, CHCl, and CCl2 with cyclopropane, 1, have been examined computationally. In all cases the lowest energy reaction between the carbene and 1 is predicted to be C−H insertion. In the reaction of CH2 with 1, the transition state for C−C insertion leading to cyclobutane is 1.7 kcal/mol higher in enthalpy than the transition state for C−H insertion at the G3B3 level. A pathway higher in energy than C−H insertion in the reactions of CHCl and CCl2 with 1 involves two-bond cleavages generating ethylene along with chloro and dichloroethylene, respectively.

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