Cope Elimination Reaction

A. C. Cope et al., J. Am. Chem. Soc. 71, 3929 (1949); idem et al., ibid. 75, 3212 (1953).

Formation of an olefin and a hydroxylamine by pyrolysis of an amine oxide:



Early reviews: C. H. DePuy, R. W. King, Chem. Rev. 60, 448 (1960); A. C. Cope, E. R. Trumbull, Org. React. 11, 317-493 passim (1960). Synthetic application: E. Tojo et al., Heterocycles 27, 2367 (1988). Mechanistic study: R. D. Bach, M. L. Braden, J. Org. Chem. 56, 7194 (1991). Methods development: A. D. Woolhouse, J. Heterocyclic Chem. 30, 873 (1993). Synthetic applications of the reverse reaction (retro-Cope elimination): E. Ciganek, J. Org. Chem. 55, 3007 (1990); M. B. Gravestock et al., Chem. Commun. 1993, 169. Cf. Chugaev Reaction; Hofmann Degradation.