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Molecules 2011, 16(9), 7267-7287; doi:10.3390/molecules16097267
Article

Cyclization vs. Cyclization/Dimerization in o-Amidostilbene Radical Cation Cascade Reactions: The Amide Question

1, 1, 1, 2, 3, 4, 5 and 1,*
Received: 5 August 2011; in revised form: 16 August 2011 / Accepted: 17 August 2011 / Published: 25 August 2011
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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 FeCl3 promoted cyclization to produce only indoline, while n-butyramidostilbene, under the same conditions, produces both indoline and bisindoline.
Keywords: stilbene; indoline; bisindoline; FeCl3 stilbene; indoline; bisindoline; FeCl3
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Kee, C.H.; Ariffin, A.; Awang, K.; Noorbatcha, I.; Takeya, K.; Morita, H.; Lim, C.G.; Thomas, N.F. Cyclization vs. Cyclization/Dimerization in o-Amidostilbene Radical Cation Cascade Reactions: The Amide Question. Molecules 2011, 16, 7267-7287.

AMA Style

Kee CH, Ariffin A, Awang K, Noorbatcha I, Takeya K, Morita H, Lim CG, Thomas NF. Cyclization vs. Cyclization/Dimerization in o-Amidostilbene Radical Cation Cascade Reactions: The Amide Question. Molecules. 2011; 16(9):7267-7287.

Chicago/Turabian Style

Kee, Chin Hui; Ariffin, Azhar; Awang, Khalijah; Noorbatcha, Ibrahim; Takeya, Koichi; Morita, Hiroshi; Lim, Chuan Gee; Thomas, Noel Francis. 2011. "Cyclization vs. Cyclization/Dimerization in o-Amidostilbene Radical Cation Cascade Reactions: The Amide Question." Molecules 16, no. 9: 7267-7287.


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