The Relative Reactivities of the Seven Nuclear Positions of Isoquinoline to Free-Radical Phenylation

Abstract

Free-radical phenylation of isoquinoline has been effected both by photolysis of phenylthallium(III) di(trifluoroacetate) and by the action of pentyl nitrite on aniline. Analysis of the isomeric phenyl isoquinoline mixture by g.l.c. and h.p.l.c. established the reactivity order in the isoquinoline nucleus to be 1 > 5 > 8 > 4 > 3,6,7. This experimental order is compared with the eight published theoretical predictions, none of which is correct.