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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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 |
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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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1777407386698383360 |