[2+ 2] Cycloaddition reaction of cycloheptatriene with dichloroketene. A novel and efficient synthetic strategy for the synthesis of 2-hydroxyazulene

R Yokoyama, S Ito, M Watanabe, N Harada…

Index: Yokoyama; Ito; Watanabe; Harada; Kabuto; Morita Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 18 p. 2257 - 2261

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Citation Number: 2

Abstract

The reaction of cycloheptatriene with dichloroketene, generated by the treatment of trichloroacetyl chloride with activated zinc in dry diethyl ether, affords 9, 9-dichlorobicyclo [5.2. 0] nona-2, 4-dien-8-one 2 as a major product together with 3′, 3′, 9, 9- tetrachlorospiro (bicyclo [5.2. 0] nona-2, 4-diene-8, 2′-oxetan)-4′-one 3. Structure 3 is elucidated by the X-ray crystallographic analysis of its partially reduced product. Lactone 3 ...