HOMOLYTIC SUBSTITUTION OF HETEROAROMATIC COMPOUNDS .I. HOMOLYTIC BENZYLATION OF PYRIDINE QUINOLINE AND ISOQUINOLINE IN ACIDIC AND NON-ACIDIC MEDIA

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 non-acidic solution, and the reactivities of positions 2 and 4 in quinoline and position 1 in isoquinoline are enhanced in acidic media.