Acid-catalyzed rearrangements of humulene

WG Dauben, JP Hubbell…

Index: Dauben,W.G. et al. Journal of Organic Chemistry, 1975 , vol. 40, # 4 p. 479 - 485

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Citation Number: 31

Abstract

Upon extended treatment with acid, the sesquiterpene humulene yielded 20-25% a- caryophyllene alcohol and 70-75% mainly a new bicyclic sesquiterpene hydrocarbon. The structure of the material, as well as a series of its precursors, was established. The mechanism of the transformation was shown to proceed via a series of stepwise rearrangements.