The rates of deprotonation of some p-cyclopropyltoluene derivatives in search for the effect of the conformation of cyclopropyl groups on the stabi

Abstract

p-Cyclopropyltoluene and 2-cyclopropylmesitylene have been prepared and the rates of base-catalyzed H-D exchange of the benzylic hydrogen atoms, para positioned with respect to the cyclopropyl group, have been compared with those of suitable model compounds. The results are in accord with earlier findings, where a cyclopropyl group exerts more stabilization to the carbanionic centres than do other alkyl groups. The present results suggest that this stabilization is independent of the conformation of the cyclopropyl group (perpendicular or bisected) with respect to the carbanionic centre.