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

Ariffin, Azhar and Thomas, N.F. and Kee, C.H. and Morita, H. and Awang, K. and Noorbatcha, I. and Takeya, K. and Lim, C.G. (2011) Cyclization vs. cyclization/dimerization in o-Amidostilbene Radical Cation Cascade reactions: the amide question. Molecules, 16 (9). pp. 7267-7287. ISSN 1420-3049, DOI https://doi.org/10.3390/molecules16097267.

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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, isobutyramido-stilbene undergoes FeCl(3) promoted cyclization to produce only indoline, while n-butyramidostilbene, under the same conditions, produces both indoline and bisindoline.

Item Type:	Article
Funders:	UNSPECIFIED
Additional Information:	Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords:	Amides/*chemistry; Catalysis; Cations; Chlorides/chemistry; Cyclization; Dimerization; Ferric compounds/chemistry; Free radicals/chemistry; Indoles/chemical synthesis; Models, chemical; Molecular conformation; Molecular structure; Oxidation-reduction; Stereoisomerism; Stilbenes/*chemistry;
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science > Department of Chemistry
Depositing User:	Miss Malisa Diana
Date Deposited:	03 Jul 2013 04:17
Last Modified:	27 Aug 2019 06:22
URI:	http://eprints.um.edu.my/id/eprint/8092

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