Canadian Journal of Chemistry

Acid catalysed rearrangements of 8, 8-dimethyl-2, 3-homotropone

RF Childs, A Varadarajan

Index: Childs, Ronald F.; Varadarajan, Aravamuthan Canadian Journal of Chemistry, 1981 , vol. 59, p. 3252 - 3255

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Citation Number: 4

Abstract

The Brønsted and Lewis acid catalysed rearrangements of 8, 8-dimethyl-2, 3-homotropone, 2, have been examined. Four major products have been identified: 2-isopropyltropone, 6; isobutyrophenone, 7; 2-isobutenylphenol, 8; and 8, 8-dimethylbicyclo [3.2. 1]-octa-3, 6-dien- 2-one, 5. The relative amounts of these products differ very markedly as the acid medium changes. Mechanisms are proposed to account for these reactions.

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