The addition of dichlorocarbene to norbornylene yielded 3,3-dichloro-ezo-tricyclo [3.2. l.02,4] octane (11) which rearranged with great facility to ezo-3,4-dichlorobicyclo[3.2.l]oct-2-ene (111). The nuclear magnetic resonance spectra allowed configurational assignments and are presented in detail. The rearrangement of I1 to I11 exhibited first-order kinetics a t 22" when carried out in carbon tetrachloride, methylene chloride, acetone, and acetonitrile, the rate being strongly affected by the dielectric constant of the solvent. Preliminary observations on the less clear-cut reaction of dichlorocarbene with norbornadiene are reported.
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