Dibenzo diazocine, 6,12-dichloro

Dibenzo[b,/][l,5]diazocine, tetrahydro-conformation, 7, 704 Dibenzo[b,/][l,4]diazocinediones synthesis, 7, 675 Dibenzodioxin, 2,7-dichloro-toxicity, 3, 992 Dibenzodioxin, hexachloro-toxicity, 3, 992 Dibenzodioxin, octachloro-toxicity, 3, 992... 

Condensations of anthranilic acid derivatives lead to the 6,12-diamino- and 6,12-dioxo-dibenzodiazocines, and the dichloro compound (279) is available from the latter (54JCS3429). Reduction of (279) via the dihydrazino compound was used to prepare the parent dibenzo[6,/][l,5]diazocine (280) (67CC1077). The NMR value (5 8.53 p.p.m.) of the 6(12) proton is indicative of the diazocine structure, presumably in a tub form, rather than the valence isomeric dibenzodiazapentalene (281). 

A number of 1,4-diazocines have reacted to form imidazoles and fused-ring analogs. Beckmann rearrangement of the dioxime 171 yielded isoindolo-benzimidazole 172 (R = Cl, R = H) or 172 (R = H, R = Cl), most likely via rearrangement of an initially formed dichloro- 57 (57JCS1900). Dibenzo-diazocinedione 57, when heated with phosphorus pentachloride, afforded an... 

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