Carroll Rearrangement

M. F. Carroll, J. Chem. Soc. 1940, 704; 1941, 507; W. Kimel, A. C. Cope, J. Am. Chem. Soc. 65, 1992 (1943).

Preparation of γ,δ-unsaturated ketones by base-catalyzed reaction of allylic alcohols with β-ketoesters or thermal rearrangement of allyl acetoacetates:



Detailed experimental: S. R. Wilson, C. E. Augelli, Org. Syn. 68, 210 (1990). Synthetic applications: A. V. Echavarren et al., Tetrahedron Letters 32, 6421 (1991); N. Ouvrard et al., ibid. 34, 1149 (1993). Cf. Claisen Rearrangement.