Cyclization vs. Cyclization/Dimerization in o-Amidostilbene Radical Cation Cascade Reactions: the Amide question

Chin , Hui Kee and Ariffin, Azhar and Awang , Khalijah and Ibrahim Ali , Noorbatcha and Takeya, Koichi and Morita, Hiroshi and Chuan , Gee Lim and Thomas, Noel Francis (2011) Cyclization vs. Cyclization/Dimerization in o-Amidostilbene Radical Cation Cascade Reactions: the Amide question. Molecules , 16 (9). pp. 7267-7287. ISSN 1420-3049

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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, isobutyramidostilbene undergoes FeCl3 promoted cyclization to produce only indoline, while n-butyramidostilbene, under the same conditions, produces both indoline and bisindoline. Keywords: stilbene; indoline; bisindoline; FeCl3

Item Type:	Article (Journal)
Additional Information:	3704/2047
Uncontrolled Keywords:	stilbene; indoline; bisindoline; FeCl3
Subjects:	Q Science > QD Chemistry
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button):	Kulliyyah of Engineering > Department of Biotechnology Engineering
Depositing User:	Prof. Dr. Ibrahim Ali Noorbatcha
Date Deposited:	18 Nov 2011 15:10
Last Modified:	06 May 2012 17:56
URI:	http://irep.iium.edu.my/id/eprint/2047

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