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Paper | Special issue | Vol 61, No. 1, 2003, pp.237-245
Published online, 15th July, 2003
DOI: 10.3987/COM-03-S23
Generation and Reactions of 3-Phenyl-7,8-dehydro-1-azaazulene

Noritaka Abe,* Masao Yoshitsugu, Hiroyuki Fujii, and Akikazu Kakehi

*Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi 753-8512, Japan

Abstract

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 and 7-phenyl-3H-3a,3c-dihydro-1-aza-3-oxacyclopenta[3,4]cyclobuta[1,2-e]azulene as cycloadducts.