Die Solvolyse von exo- und endo-3-Chlor-bicyclo[3.2.1]octan

The rates of solvolysis of exo and endo 3-chloro bicyclo3.2.1]octane 1a and 2a have been measured in 80 vol.% aqueous ethanol. The axial endo chloride reacts 263 times as fast as the equatorial exo epimer. This remarkably large rate difference is ascribed to sterically accelerated ionisation of the axial endo epimer due to the ethano bridge.