Homolytic substitution of heteroaromatic compounds. Part I. Homolytic benzylation of pyridine, quinoline, and isoquinoline in acidic and non-acidic media

Abstract

The effect of N-protonation on the homolytic benzylation of pyridine, quinoline, and isoquinoline has been studied. Pyridine is not benzylated in non-acidic solution, but 2- and 4-benzylpyridine are formed in acidic media. Benzylation of quinoline at positions 2 and 4, and isoquinoline at positions 1, 3, and 4, occurs to a small extent in nonacidic solution, and the reactivities of positions 2 and 4 in quinoline and position 1 in isoquinoline are enhanced in acidic media.