Reactions of ionized 4-benzyl-2-methyl-1,2,3,4-tetrahydroisoquinolines in the gas phase

Article abstract of DOI:10.1002/ardp.19923251209

The M^+. of 4-Benzyl-1,2,3,4-2-methyl-tetrahydroisoquinoline (1) decomposes by competing loss of H^.- or H₃C^.-radicals, of H₃C-NH₂, C₆H₆ and C₇H₈, respectively, or by RDA-fission. The fragmentation mechanisms are studied on the specifically deuterated analogues 2-8. The elimination of C₆H₆ and C₇H₈ is preceded by extensive H/D-exchange, especially between the positions 1, 4, the benzylic methylene group, and the aromatic positions (pos. 5, 8, and phenyl).