16714-24-2Relevant academic research and scientific papers
3H-Azepines and Related Systems. Part 2. The Photolyses of Aryl Azides Bearing Electron-withdrawing Substituents
Purvis, Roger,Smalley, Robert K.,Suschitzky, Hans,Alkhader, Mohamed A.
, p. 249 - 254 (2007/10/02)
The photolyses of ortho-substituted aryl azides (o-XC6H4N3 where X = CONHNH2, CONHN=CHAr, NO2, CN, CF3, SO2OMe, SO2NH2, or SO2Ph) in methanol-tetrahydrofuran solution are described.With X = CF3 or CONHN=CHAr, 3-substituted 2-methoxy-3H-azepines are products, while in other cases polymeric products, amines or mixtures of isomeric azepines are obtained.The product from the photolysis of o-azidophenyl phenyl sulphoxide (X = SOPh) is identified tentatively (n.m.r. evidence) as 7-methoxy-2-phenylsulphinyl-3H-azepine.In contrast, methyl p-azidobenzoate and p-cyanophenyl azide yield the corresponding 5-substituted 2-methoxy-3H-azepines, whereas methyl m-azidobenzoate yields only methyl 2-methoxy-3H-azepine-6-carboxylate.Irradiation of methyl o-azidobenzoate in aqueous tetrahydrofuran gives 1,3-dihydro-3-methoxycarbonyl-2H-azepin-2-one.
