Tetrahedron

Electrocyclic aromatic substitution by nitrile ylides to give 3H-2-benzazepines: substituent effects and mechanism

PW Groundwater, JT Sharp

文献索引：Groundwater, Paul W.; Sharp, John T. Tetrahedron, 1992 , vol. 48, # 37 p. 7951 - 7964

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被引用次数: 15

摘要

Benzonitrile 3, 3-diarylallyl nitrile ylides (16), generated by the base-induced dehydrochlorination of imidoyl chlorides, cyclised by 1, 7-ring closure to give 3H-2- benzazepines eg (19), in contrast to analogous diazo-compounds (1) which prefer 1, 5- electrocyclisation. Asymmetrically placed substituents [R in (16b–e)] favour substitution at the ortho (2′) position irrespective of their polar electronic effects. Deuterium labelling ...