No abstract

The mono-o-azidobenzoates ( I a -c ) of mono-, di-, and tri-ethylene glycol, on photolysis in methanoltetrahydrofuran, yield the corresponding glycol monoesters ( 2 a -c ; R = H) of 2-methoxy-3H-azepine-3-carboxylic acid. A bis-3H-azepine-3-carboxylate (4a) is obtained from ethylene glycol di-oazidobenzoate (3a). Similarly, bis-3H-azepine-3-carboxamides ( I 2)-(I 4) are obtained by ringexpansion of the di-o-azidobenzoyl derivatives of ethylene, and 0-and p-phenylene diamines. Photolysis of the o-azidobenzoates of 2-ethoxyethanol (6a) and diethylene glycol monomethyl ether (6b) in mono-or di-ethylene glycol, or their monoalkyl ethers and tetrahydrofuran, produces 2-alkoxy-3H-azepine-3-carboxylates (5a), (5b), ( 7 ) , and (8) one of which, (8), has metal cation complexing properties. Irradiation of phydroxyethyl o-azidobenzoate (1 a) in tetrahydrofuran furnishes a diazepino 14-crown-4 analogue (1 8), whereas on spray pyrolysis indazolo[2,1 -a]indazole-6,12-dione (20) is obtained.