Cyclization vs. Cyclization/Dimerization in o-Amidostilbene Radical Cation Cascade Reactions: The Amide Question
oleh: Noel Francis Thomas, Chuan Gee Lim, Hiroshi Morita, Koichi Takeya, Khalijah Awang, Ibrahim Noorbatcha, Azhar Ariffin, Chin Hui Kee
| Format: | Article |
|---|---|
| Diterbitkan: | MDPI AG 2011-08-01 |
Deskripsi
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.