Cope Rearrangement; Oxy-Cope Rearrangement

A. C. Cope et al., J. Am. Chem. Soc. 62, 441 (1940).

Highly stereoselective [3,3]-sigmatropic rearrangement of 1,5-dienes; “all-carbon” equivalent of the Claisen rearrangement, q.v.:

When R = OH, the transformation is referred to as the oxy-Cope rearrangement: J. Berson, M. Jones, ibid. 86, 5019 (1964).

Reviews: S. J. Rhodds, N. R. Raulins, Org. React. 22, 1-252 (1975); S. R. Wilson, ibid. 43, 93-250 passim (1993); R. K. Hill, Comp. Org. Syn. 5, 785-826 (1991). Review of hetero-Cope rearrangements: S. Blechert, Synthesis 1989, 71-82. Brief review of synthetic applications: K. Durairaj, Curr. Sci. 66, 917-922 (1994).