Naphth azepines

Subsequently, it was shown that cyclopentadienones are very efficient in trapping 2//-azirines formed transiently during the thermolysis of vinyl azides,109 and that 3//-azepines may be formed by heating the vinyl azide directly in the presence of the cyclopentadienone rather than with the often foul-smelling 2//-azirine.31,109 An example of this procedure is the preparation of the dihydro-3/f-naphth[2,l-fe]azepine 29 by thermolysis of 4-azido-l,2-dihydronaph-thalene (28) with 2,5-dimethyl-3,4-diphenylcyclopentadienone in refluxing toluene. 

Similar reactions with 2-azidoanthracenes 12 produce l//-naphth[2,3-c]azepines 13.174,175... 

Cumulative Index of Heterocyclic Systems Naphth[2,3- ]azepine (1188)... 

Azidoanthracene irradiated 0.5 hr. with 350-410 nm light in a 1 1 mixture of methanolic K-methoxide and dioxane, then refluxed briefly or left overnight at room temp. 3-methoxy-lH-naphth[2,3-c]azepine. Y almost 100%. F. e. s. J. Rigaudy, C. Igier, and J. Barcelo, Tetrah. Let. 1975, 3845. 

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