Hydrogen chloride treatment of quinolinic aminoxyls. Part 2. Crystal structures of 6-chloro-1,2-dihydro-2,2-diphenyl- and 6,8-dichloro-1,2-dihydro-2,2-diphenylquinoline

Abstract

Quinolinic aminoxyls 1a–c, whose structures are similar to those formed from 1,2-dihydroquinolines, used as antioxidants and photostabilizers in plastics and rubbers, under hydrogen chloride treatment led to the formation of the corresponding mono-(2) and di-chlorinated (3) amines. The structures of the isolated compounds have been determined by X-ray analysis of 6-chloro-1,2-dihydro-2,2-diphenyl- and 6,8-dichloro-1,2-dihydro-2,2-diphenylquinoline (2a and 3a). The mechanisms of chlorination and deoxygenation are discussed on the basis of the experimental results and literature reports.