Cyclodehydrogenation of 3-Isopropenyl-and 3-(1-Phenylvinyl)-tropolones to 8H-Cyclohepta [b] furan-8-one Derivatives

K Imafuku, K Yamaguchi, H Matsumura

Index: Imafuku, Kimiaki; Yamagushi, Kazuko; Matsumura, Hisashi Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 3 p. 745 - 747

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Citation Number: 7

Abstract

3-(1-Phenylvinyl) tropolone (3b) was prepared by the hydrolysis of cycloadducts of 6-methyl- 6-phenylfulvene with dichloroketene. 3-Isopropenyltropolone and 3b were treated with 2, 3- dichloro-5, 6-dicyano-p-benzoquinone or performic acid to give 3-methyl-and 3-phenyl-8H- cyclohepta [b] furan-8-one, respectively. Reaction of 3b with hydrazoic acid afforded an unexpected 3-acetyltropolone.