Intramolecular nitrene insertions into aromatic and heteroaromatic systems. Part III. Photochemical decomposition of azido-indanes and azido-1,2-dihydrobenzocyclobutenes
Abstract
Photochemical decomposition of 4-azidoindane (3) in diethylamine gave 5-diethylamino-1,2,3,6-tetrahydro-4-aza-azulene (22), 4-diethylamino-1,2,3,3a-(19), and 4-diethylamino-1,2,3,8-tetrahydro-5-aza-azulene (20). Similar decomposition of 5-azidoindane (7) gave a mixture of 5-diethylamino-1,2,3,4-tetrahydro-6-aza-azulene (26) and 6-diethylamino-1,2,3,7-tetrahydro-5-aza-azulene (24). From 4-azido-1,2-dihydrobenzocyclobutene (11) a good yield of 4-diethylamino-1,2-dihydro-3H-5-azacyclobutacycloheptene (30) was obtained; 2-azidobiphenylene (13) gave no azepines, only 2-aminobiphenylene (31) and a little 2,2′-azobisbiphenylene (35).