Chugaev Reaction (Tschugaeff Olefin Synthesis)

L. Chugaev (Tschugaeff), Ber. 32, 3332 (1899).

Formation of olefins from alcohols without rearrangement through pyrolysis of the corresponding xanthates via cis-elimination:



C. H. DePuy, R. W. King, Chem. Rev. 60, 444 (1960); H. R. Nace, Org. React. 12, 57 (1962); K. Harano, T. Taguchi, Chem. Pharm. Bull. Japan 20, 2357 (1972); J. March, Advanced Organic Chemistry (John Wiley & Sons, NY, 1992) 1014-1015. Synthetic applications: X Fu, J. M. Cook, Tetrahedron Letters 31, 3409 (1990); P. S. Ray, M. J. Manning, Heterocycles 33, 1361 (1994). Cf. Cope Elimination Reaction.