TY - JOUR
T1 - Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates
T2 - Formation and characterization of 2H-, 3H- and 4H-azepines
AU - Satake, Kyosuke
AU - Okuda, Ryoichi
AU - Hashimoto, Michiaki
AU - Fujiwara, Yasusi
AU - Okamoto, Hideki
AU - Kimura, Masaru
AU - Morosawa, Shiro
PY - 1994/12/1
Y1 - 1994/12/1
N2 - Demethoxycarbonylation of methyl 2,5-di-tert-butyl-1H-azepine-1-carboxylate using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave 3H-azepines. Under similar conditions, methyl 3,6-ditert-butyl-1H-azepine-1-carboxylate gave not only the 3H-azepine but also the isomerized 2H- and 4H-azepines. Application of the reaction to dimethyl and diisopropyl substituted 1H-azepines showed that bulky alkyl group substitution stabilizes the seven-membered azatriene system. The thermal behaviour of the di-tert-butyl substituted azepines is discussed.
AB - Demethoxycarbonylation of methyl 2,5-di-tert-butyl-1H-azepine-1-carboxylate using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave 3H-azepines. Under similar conditions, methyl 3,6-ditert-butyl-1H-azepine-1-carboxylate gave not only the 3H-azepine but also the isomerized 2H- and 4H-azepines. Application of the reaction to dimethyl and diisopropyl substituted 1H-azepines showed that bulky alkyl group substitution stabilizes the seven-membered azatriene system. The thermal behaviour of the di-tert-butyl substituted azepines is discussed.
UR - http://www.scopus.com/inward/record.url?scp=37049083977&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=37049083977&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:37049083977
SN - 1472-7781
SP - 1753
EP - 1757
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 13
ER -