HETEROLYSIS OF N-CHLORO-1,2,3,4-TETRAHYDRO-1,4-IMINONAPHTHALENES AND RELATED SYSTEMS; EFFECTS OF STRUCTURE AND SOLVENT ON REACTION PATHWAYS

Article abstract of DOI:10.1016/S0040-4039(00)84913-8

Replacement of hydrogen by methyl at the 1,4-positions of 1,2,3,4-tetrahydro-1,4-iminonaphtalenes substancially modifies the Ag(I)-catalysed solvolytic behaviour of this system giving tetrahydrobenzazepine derivatives; small amounts of methanol in non-polar solvents have a profound effect favouring heterolytic, rather than homolytic, N-Cl cleavage.Methanoquinolines are produced via secondary rearrangement.Bridgehead methyl substituents also divert the reactions of N-chloro-1,4-dihydro-1,4-iminonaphtalenes, leading to quinoline derivatives.