Cyclization vs. cyclization/dimerization in o-Amidostilbene Radical Cation Cascade reactions: the amide question

Cyclization vs. cyclization/dimerization in o-Amidostilbene Radical Cation Cascade reactions: the amide question

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 f...

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Bibliographic Details
Main Authors: Ariffin, Azhar, Thomas, N.F., Kee, C.H., Morita, H., Awang, K., Noorbatcha, I., Takeya, K., Lim, C.G.
Format: Article
Language:English
Published: 2011
Subjects:
QD Chemistry
Online Access:http://eprints.um.edu.my/8092/1/Kee-2011-Cyclization_vs._Cycl.pdf
http://eprints.um.edu.my/8092/
http://www.mdpi.com/1420-3049/16/9/7267/pdf
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Institution: Universiti Malaya
Language: English
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Summary: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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