Reactions of N-quaternary 1-phenyl-3,4-dihydroisoquinolinium compounds with nucleophiles--products and their isomerism--part 2

A series of substituted 1-phenyl-3,4-dihydroisoquinolinium compounds was treated with O-, C- and N-nucleophilic agents in order to study ring-chain isomerism of the products. With methanolate carbinolamine ethers and with cyanide pseudocyanides as cyclic species resulted from these iminium salts. Electronic and steric differently substituted dihydroisoquinoline compounds reacted with hydroxylamine under ring opening generally to amine oximes predominantly in their Z-configuration. A cyclic isomer substituted with a hydroxylamine group--also in equilibrium in solution--could be excluded. With O-methylhydroxylamine a similar reaction gave rise to amine oxime methyl ethers only. 4-Phenylsemicarbazide and 4-nitrophenylhydrazine in pyridine produced the ring opened hydrazone derivatives.