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

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

Creators Abe Noritaka

Creators Yoshitsugu Masao

Creators Fujii Hiroyuki

Creators Kakehi Akikazu

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.

[ISSN]0385-5414

[NCID]AA00663739