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The kinetics of solvolysis of the epimeric tricyclo0^'^]deca-2,4'-diene-10-carbinyl 3f5-dinitro'benzoates, as well as their monoolefin and saturated derivatives, were determined in aqueous acetone. It was found that the anti series solvolyzed faster than the svn analogs. The rate constants were employed to calculated the equilibrium constant for the monosuhstituted cycloheptatriene-norcaradiene equi­ librium; the estimated energy barrier was ca. 4.5 kcal/mole. The second part concerns the study of the silver-assisted hydrolysis (in aqueous acetone) and buffered acetolysis of some monobromoand dihalopropellanes. The major products formed upon solvolysis of the 10,10-dibromo[4o3.1]propellanes indicated that the reactions occurred via bridgehead olefins transoid in a 7-membered ring, followed by protonation and rearrangement» The solvolysis of ll,ll-dihalo[4.4.l]pro13 pellanes were also shown, via the use of ^C-labeling at the position, to proceed via the intermediacy of a bridgehead olefin species, contrary to ear-.ier conjecture. The relative difficulty of generating a bridgehead double bond transoid in a 6-membered ring was demonstrated by the minor amount of such products isolated from the hydrolysis of 9,9-dlbromo[3.3.1]propellane. Comparison of the percentage of products which arose from the bridgehead olefin intermediates with

I. The cycloheptatriene-norcaradiene equilibrium problem: Solvolysis of norcaradienylcarbinyl derivatives. II. Solvolytic formation of bridgehead olefins. III Studies of certain cyclopropyl anions and radicals