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 |
| Publication status | Published - Oct 1 2003 |
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ASJC Scopus subject areas
- Organic Chemistry
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Plausible mechanism for the formation of 2-methoxy-2H-azepine derivatives from 3H-azepines using bromine and NBS. / Satake, Kyosuke; Cordonier, Christopher; Kubota, Yasuhiro; Jin, Yuexian; Kimura, Masaru.
In: Heterocycles, Vol. 60, No. 10, 01.10.2003, p. 2211-2215.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Plausible mechanism for the formation of 2-methoxy-2H-azepine derivatives from 3H-azepines using bromine and NBS
AU - Satake, Kyosuke
AU - Cordonier, Christopher
AU - Kubota, Yasuhiro
AU - Jin, Yuexian
AU - Kimura, Masaru
PY - 2003/10/1
Y1 - 2003/10/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0142027861&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0142027861&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0142027861
VL - 60
SP - 2211
EP - 2215
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 10
ER -