The Isomerization of Thujone1

RH Eastman, AV Winn

Index: Eastman,R.H.; Winn,A.V. Journal of the American Chemical Society, 1960 , vol. 82, p. 5908 - 5914

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Citation Number: 17

Abstract

Among the cleavages of the bicyclo [3.1. 0]-hexane system, 2 that of thujone (I) by mineral acids presents an anomaly since the reporteda formation of carvotanacetone (11) involves a violation of the Markownikoff rule as applied to the opening of three-membered rings by acidic agents4 Evidence is presented here to the effect that carvotanacetone (11) is not a product of the acid-catalyzed cleavage; that the products are those pre-