Cyclization vs. cyclization/dimerization in o-amidostilbene radical cation cascade reactions: the amide question

邻氨基二苯乙烯自由基阳离子级联反应中的环化与环化/二聚化:酰胺问题

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作者:Chin Hui Kee, Azhar Ariffin, Khalijah Awang, Ibrahim Noorbatcha, Koichi Takeya, Hiroshi Morita, Chuan Gee Lim, Noel Francis Thomas

Abstract

The n-butyramido, isobutyramido, benzamido, and furancarboxamido functions profoundly modulate the electronics of the stilbene olefinic and NH groups and the corresponding radical cations in ways that influence the efficiency of the cyclization due presumably to conformational and stereoelectronic factors. For example, isobutyramido- stilbene undergoes FeCl(3) promoted cyclization to produce only indoline, while n-butyramidostilbene, under the same conditions, produces both indoline and bisindoline.

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