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...

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Main Authors: Chin , Hui Kee, Ariffin, Azhar, Awang , Khalijah, Ibrahim Ali , Noorbatcha, Takeya, Koichi, Morita, Hiroshi, Chuan , Gee Lim, Thomas, Noel Francis
Format: Article
Language:English
Published: MDPI 2011
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spelling iium-20472012-05-06T09:56:01Z http://irep.iium.edu.my/2047/ Cyclization vs. Cyclization/Dimerization in o-Amidostilbene Radical Cation Cascade Reactions: the Amide question Chin , Hui Kee Ariffin, Azhar Awang , Khalijah Ibrahim Ali , Noorbatcha Takeya, Koichi Morita, Hiroshi Chuan , Gee Lim Thomas, Noel Francis 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, 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 MDPI 2011-08-25 Article PeerReviewed application/pdf en http://irep.iium.edu.my/2047/1/molecules-16-07267.pdf 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 http://www.mdpi.com/1420-3049/16/9/7267 DOI:10.3390/molecules16097267
repository_type Digital Repository
institution_category Local University
institution International Islamic University Malaysia
building IIUM Repository
collection Online Access
language English
topic QD Chemistry
spellingShingle QD Chemistry
Chin , Hui Kee
Ariffin, Azhar
Awang , Khalijah
Ibrahim Ali , Noorbatcha
Takeya, Koichi
Morita, Hiroshi
Chuan , Gee Lim
Thomas, Noel Francis
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, 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
format Article
author Chin , Hui Kee
Ariffin, Azhar
Awang , Khalijah
Ibrahim Ali , Noorbatcha
Takeya, Koichi
Morita, Hiroshi
Chuan , Gee Lim
Thomas, Noel Francis
author_facet Chin , Hui Kee
Ariffin, Azhar
Awang , Khalijah
Ibrahim Ali , Noorbatcha
Takeya, Koichi
Morita, Hiroshi
Chuan , Gee Lim
Thomas, Noel Francis
author_sort Chin , Hui Kee
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
publisher MDPI
publishDate 2011
url http://irep.iium.edu.my/2047/
http://irep.iium.edu.my/2047/
http://irep.iium.edu.my/2047/
http://irep.iium.edu.my/2047/1/molecules-16-07267.pdf
first_indexed 2023-09-18T20:09:34Z
last_indexed 2023-09-18T20:09:34Z
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