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

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.

SUBMITTER: Kee CH

PROVIDER: S-EPMC6264379 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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

Kee Chin Hui CH Ariffin Azhar A Awang Khalijah K Noorbatcha Ibrahim I Takeya Koichi K Morita Hiroshi H Lim Chuan Gee CG Thomas Noel Francis NF

Molecules (Basel, Switzerland) 20110825 9

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 bisindol ...[more]

PMID: 21869754

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