Chemistry of 8-substituted 1-naphthylmethylenes and 2-substituted benzylidenes. A simple entry to 1H-cyclobuta [de] naphthalenes

RJ Bailey, P Card, H Shechter

Index: Bailey, R. J.; Card, P. J.; Shechter, H. Journal of the American Chemical Society, 1983 , vol. 105, # 19 p. 6096 - 6103

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Citation Number: 62

Abstract

Abstract: Study has been made of neighboring heteroatom interaction in thermolysis and photolysis of proximally substituted aryldiazomethanes. Thus, (8-bromo-1-naphthyl)- (la), (8-iodo-1-naphthyl )- (lb), and (5,8-dichloro- 1-naphthy1)diazomethane (IC) isomerize at 132 OC to 9-bromo- (Ma), 9-iodo- (18b), and 6,9-dichloro-3H-benz[e]indazoles (18c). Indazoles 18a and 18b are reduced by lithium aluminum hydride to 3H-benz[e]indazole (21), identical with that from ...