Journal of the American Chemical Society

Halogenated ketenes. XXII. Solvolysis of alkylhaloketene-cyclopentadiene adducts to 2-alkyltropones

WT Brady, JP Hieble

Index: Brady,W.T.; Hieble,J.P. Journal of the American Chemical Society, 1972 , vol. 94, p. 4278 - 4284

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Citation Number: 19

Abstract

Abstract: The cycloadducts of alkylhaloketenes and cyclopentadiene were solvolyzed in aqueous base to produce 2-alkyltropones. A competing Favorskii-type ring contraction reaction also occurs producing 6-alkyl-6-carboxybicyclo [3.1. O] hex-2-enes. The 2- alkyltropones are produced only from the endo-alkyl isomer of the alkylhaloketene- cyclopentadiene adduct, The relative amounts of 2-alkyltropone and ring contraction ...