Heterocyclic ambident nucleophiles. II. The alkylation of adenine

Abstract

The alkylation of un-ionized adenine by a variety of primary alkyl halides under standardized, common conditions (HCONMe₂, 100º) was investigated. The alkylation pattern (N 1 : N 3 : N 7 : N 9) was found to be relatively insensitive to changes in the nature of the alkylating agent, except for cases involving benzyl chloromethyl ether and chloromethyl pivalate. An interpretation of these patterns in terms of modern ambient nucleophile reactivity concepts and variable S_N2 transition state structures is presented.