Substitution reactions in cyclic systems. Displacement reactions of some sterically hindered tosylates

Nucleophilic attack upon cyclopentyl, endo-2-norbornyl, endo-5,6-trimethylene-endo-2-norbornyl, endo-5,6-trimethylene-endo-8-norbornyl, and endo-5,6-trimethylene-endo-9-norbornyl cyclic tosylates has been studied. No rearrangement occurred during the reactions. The relative rates of displacement have been found to be very similar to the reactivity observed for solvolyses. Increased steric interaction by alkyl groups on the leaving group causes the displacement rate to decrease.