Generation and reactions of 3-phenyl-7,8-dehydro-1-azaazulene

3-Phenyl-7,8-dehydro-1-azaazulenes were generated by the treatment of 8-bromo-3-phenyl-1-azaazulenes with potassium t-butoxide in DMSO or in THF in the presence of 16-crown-8-ether, and trapped with diphenylisobenzofuran as 3,7,12-triphenyl-1-aza-7,12-epoxynaphth[2,3-e] azulenes. The structure of the adduct, 2-bromo-3,7,12-triphenyl-1-aza-7,12-epoxynaphth[2,3-e]azulene, was deduced by X-Ray structure analysis. Similar treatment of 8-bromo-3-phenyl-1-azaazulene with potassium t-butoxide in the presence of furan gave 3-phenyl-1-aza-7,12-epoxynaphth[2,3-e]azulene nd 7-phenyl-3H-3a, 3c-dihydro-1-aza-3-oxacyclopenta[3,4]cyclobuta[1,2-ejazulene as cycloadducts.