The preparation and rates of deprotonation of some cyclopropylcarbinyl ketones

Abstract

A group of cyclopropylcarbinyl phenyl ketones has been prepared, and the rates of base-catalysed isotope exchange of the α-hydrogen atoms have been compared with those of suitable model compounds. The results support an earlier finding which suggests that a cyclopropyl group exerts little stabilisation on an adjacent carbanionic centre, whereas the effect of a vinyl group is considerable. Only small rate variations are found when the cyclopropane ring contains a phenyl or p-nitrophenyl substituent. Some novel reactions occurring during the synthesis of related polycyclic ketones are noted.