Tetrahedron

Solvolysis of N-chloro-1, 4-dihydro-1, 4-iminonaphthalenes (7-azabenzonorbornadienes); dependence of the rearrangement pathway on the configuration at nitrogen

ML Durrant, JR Malpass

Index: Durrant, Michael L.; Malpass, John R. Tetrahedron, 1995 , vol. 51, # 25 p. 7063 - 7076

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Citation Number: 9

Abstract

N-Chloro-derivatives of the 1, 4-dihydro-1, 4-iminonaphthalene (7-azabenzonorbornadiene) ring system undergo silver (I)-assisted rearrangement with participation of etheno-(syn- chloro-series) or benzo-(anti-chloro-series) π-electrons. The high barriers to inversion at nitrogen together with some control over the ratio of invertomers allow observation of a different reaction pathway for each invertomer when reactions are performed at low ...