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: | , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI
2011
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| Subjects: | |
| Online Access: | 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 |
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| Summary: | 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 |
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