Abstract
Formation of 2-bromo-4-t-butyl-7-methoxy-2H-azepine and 4-t-butyl-7-methoxy-2-succinimidyl-2H-azepine by the respective reactions of 5-t-butyl-2-methoxy-3H-azepine with bromine and NBS suggests a plausible mechanism for the conversion of 3H-azepine to 2H-azepine as 1,4-addition of an electrophile and a consequent 1,2-dehydrobromination. Different from the case of cycloheptatriene, reaction of 3H-azepine with bromine did not give any delocalized ionic species.
| Original language | English |
|---|---|
| Pages (from-to) | 2211-2215 |
| Number of pages | 5 |
| Journal | Heterocycles |
| Volume | 60 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - Oct 1 2003 |
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
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Cite this
Satake, K., Cordonier, C., Kubota, Y., Jin, Y., & Kimura, M. (2003). Plausible mechanism for the formation of 2-methoxy-2H-azepine derivatives from 3H-azepines using bromine and NBS. Heterocycles, 60(10), 2211-2215. https://doi.org/10.3987/COM-03-9851