Tetrahedron letters

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

JW Davies, JR Malpass, RE Moss

Index: Davies, John W.; Malpass, John R.; Moss, Richard E. Tetrahedron Letters, 1986 , vol. 27, # 34 p. 4071 - 4074

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Citation Number: 7

Abstract

Abstract Replacement of hydrogen by methyl at the 1, 4-positions of 1, 2, 3, 4-tetrahydro-1, 4- iminonaphthalenes 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 Full-size image (< 1 K)