Effect of a 3-phenyl substituent on the acidity of bicyclo[3.2.1]octa-2,6-diene
Abstract
3-Phenylbicyclo-octadiene (3) has undergone base-catalysed hydrogen-deuterium exchange at C-4 only slightly faster than the parent hydrocarbon, bicyclo-octadiene (4), thereby ruling out the presence of significant homoaromatic stabilization in the bicyclo-octadienyl anion (1).