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Heterolysis of N-chloro-1,2,3,4-tetrahydro-1,4-iminonaphthalenes and related systems; effects of structure and of solvent on reaction pathways

✍ Scribed by John W. Davies; John R. Malpass; Richard E. Moss

Book ID: 104218993
Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 211 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)84913-8

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✦ Synopsis

Replacement of hydrogen by methyl at the 1,4-positions of 1,2,3,4-tetrahydro-1,4iminonaphthalenes substantially 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-Eoro-1,4-dihydro-1,4_iminonaphthalenes, leading to quinoline derivatives.

As part of our interest in the structure and the inversion process at nitrogen in derivatives of the 7-azabicyclo[2.2.llheptane ring system' and in the chemistry of the derived N-chloroamines, 2 we have prepared the 1,4-dimethyl-substituted compounds (1)-( 5).3

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