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Issue 0, 1984
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3H-azepines and related systems. Part 2. The photolyses of aryl azides bearing electron-withdrawing substituents

Abstract

The photolyses of ortho-substituted aryl azides (o-XC6H4N3 where X = CONHNH2, CONHN[double bond, length half m-dash]CHAr, NO2, CN, CF3, SO2OMe, SO2NH2, or SO2Ph) in methanol–tetrahydrofuran solution are described. With X = CF3 or CONHN[double bond, length half m-dash]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.

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Article type: Paper
DOI: 10.1039/P19840000249
J. Chem. Soc., Perkin Trans. 1, 1984, 249-254

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    3H-azepines and related systems. Part 2. The photolyses of aryl azides bearing electron-withdrawing substituents

    R. Purvis, R. K. Smalley, H. Suschitzky and M. A. Alkhader, J. Chem. Soc., Perkin Trans. 1, 1984, 249
    DOI: 10.1039/P19840000249

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