Opening of Epoxides to Olefins or Halohydrins with Vanadium (II)-Tetrahydrofuran or Vanadium(III)-Tetrahydrofuran Complexes

Tsutomu Inokuchi; Hiroyuki Kawafuchi; Sigeru Torii

doi:10.1055/s-1992-21397

Synlett 1992; 1992(6): 510-512
DOI: 10.1055/s-1992-21397

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Opening of Epoxides to Olefins or Halohydrins with Vanadium (II)-Tetrahydrofuran or Vanadium(III)-Tetrahydrofuran Complexes

Tsutomu Inokuchi^* , Hiroyuki Kawafuchi, Sigeru Torii

^*Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700, Japan

Abstract

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A variety of epoxides were deoxygenated to give the corresponding alkenes through the use of a [V₂Cl₃(THF)₆]₂[Zn₂Cl₆] complex prepared from VCl₃(THF)₃ and zinc. The reaction proceeds with a partial inversion of the configuration of the acyclic cis epoxide. Treatment of the epoxides with the vanadium(III) reagent, VCl₃(THF)₃, afforded the corresponding chlorohydrins in good yields.

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