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2005
Ketone derivatives
Q 0370
Reactions of N-Quaternary 1-Phenyl-3,4-dihydroisoquinolinium Compounds
Nucleophiles — Products and Their Isomerism — Part 2. — A series of sub20- 076 with
stituted 1-phenyl-3,4-dihydroisoquinolinium compounds are treated with O-, C- and
N-nucleophilic agents in order to study the ring-chain isomerism of the products. With
methanolate (IIa) carbinolamine ethers (IIIa) and with cyanide (IIb) pseudocyanides
(IIIb) as cyclic species result from these iminium salts. Electronic and steric differently
substituted isoquinolinium salts (IV) react with hydroxylamine under ring opening generally to the oximes (V) predominantly in their Z-configuration. An exception is the
acetophenone derivative (VI) which yields a mixture of E:Z isomers. With O-methylhydroxylamine (VIIIa) or 4-nitrophenylhydrazine (VIIIb) a similar reaction leads to
ring-opened products (IX), too. The mechanism is discussed. — (MOEHRLE*, H.;
BREVES, H.; Pharmazie 60 (2005) 1, 23-35; Inst. Pharm. Chem.,
Heinrich-Heine-Univ., D-40225 Duesseldorf, Germany; Ger., Abstr. Eng.) —
H. Haber
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