title: 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.
authors.affiliation: Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia.
authors.forename: Chin Hui
authors.initials: CH
authors.lastname: Kee
authors.forename: Azhar
authors.initials: A
authors.lastname: Ariffin
authors.forename: Khalijah
authors.initials: K
authors.lastname: Awang
authors.forename: Ibrahim
authors.initials: I
authors.lastname: Noorbatcha
authors.forename: Koichi
authors.initials: K
authors.lastname: Takeya
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Morita
authors.forename: Chuan Gee
authors.initials: CG
authors.lastname: Lim
authors.forename: Noel Francis
authors.initials: NF
authors.lastname: Thomas
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D002412:Cations; D002712:Chlorides / Q000737:chemistry; D003500:Cyclization; D019281:Dimerization; D005290:Ferric Compounds / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry*
chemical_list: D000577:Amides; D002412:Cations; D002712:Chlorides; D005290:Ferric Compounds; D005609:Free Radicals; D007211:Indoles; D013267:Stilbenes; C057812:indoline; C024555:ferric chloride