Document Type
Article
Publication Date
1-1-2011
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.
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
Divisions
CHEMISTRY
Publication Title
Molecules
Volume
16
Issue
9
Additional Information
Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA