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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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
id my.um.eprints.8092
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spelling my.um.eprints.80922019-08-27T06:22:02Z http://eprints.um.edu.my/8092/ Cyclization vs. cyclization/dimerization in o-Amidostilbene Radical Cation Cascade reactions: the amide question Ariffin, Azhar Thomas, N.F. Kee, C.H. Morita, H. Awang, K. Noorbatcha, I. Takeya, K. Lim, C.G. QD Chemistry 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. 2011 Article PeerReviewed application/pdf en http://eprints.um.edu.my/8092/1/Kee-2011-Cyclization_vs._Cycl.pdf 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 http://www.mdpi.com/1420-3049/16/9/7267/pdf 10.3390/molecules16097267
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Ariffin, Azhar
Thomas, N.F.
Kee, C.H.
Morita, H.
Awang, K.
Noorbatcha, I.
Takeya, K.
Lim, C.G.
Cyclization vs. cyclization/dimerization in o-Amidostilbene Radical Cation Cascade reactions: the amide question
description 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.
format Article
author Ariffin, Azhar
Thomas, N.F.
Kee, C.H.
Morita, H.
Awang, K.
Noorbatcha, I.
Takeya, K.
Lim, C.G.
author_facet Ariffin, Azhar
Thomas, N.F.
Kee, C.H.
Morita, H.
Awang, K.
Noorbatcha, I.
Takeya, K.
Lim, C.G.
author_sort Ariffin, Azhar
title Cyclization vs. cyclization/dimerization in o-Amidostilbene Radical Cation Cascade reactions: the amide question
title_short Cyclization vs. cyclization/dimerization in o-Amidostilbene Radical Cation Cascade reactions: the amide question
title_full Cyclization vs. cyclization/dimerization in o-Amidostilbene Radical Cation Cascade reactions: the amide question
title_fullStr Cyclization vs. cyclization/dimerization in o-Amidostilbene Radical Cation Cascade reactions: the amide question
title_full_unstemmed Cyclization vs. cyclization/dimerization in o-Amidostilbene Radical Cation Cascade reactions: the amide question
title_sort cyclization vs. cyclization/dimerization in o-amidostilbene radical cation cascade reactions: the amide question
publishDate 2011
url 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
_version_ 1643688216440602624

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