The nitration of pivalophenone

Abstract

The nitration of pivalophenone (2,2-dimethyl-1-phenylpropan-1-one), which is the first reported electrophilic substitution on that substrate, gives o-, m- and p-nitropivalophenones in the percentage ratio 30:44:26. This anomalous product distribution, which differs significantly from that found for benzene rings bearing other dipolar deactivating substituents such as acetyl groups, is attributed to a sterically induced non-coplanarity of the carbonyl group, in the pivaloyl moiety, with the benzene ring.