Formation of Olefins from Alkyl Radicals with Leaving Groups in the β-Position

Article abstract of DOI:10.1021/jo00194a010

A reaction of ethanol with Fe²⁺-ethylenediaminetetraacetate (EDTA)-O2 to give ethylene is described.This olefin-forming reaction was observed with a wide variety of compounds (alcohols, halides, ethers, acetates, ethyl sulfide, and N,N-diethylaniline).Olefins were also produced with Cu⁺-O2 in acidic solution and Fe²⁺-EDTA-H2O2 and in some cases with Fe²⁺-H2O2.The effect of H⁺, H2O2, EDTA, Fe²⁺, and O2 concentrations on olefin formation was investigated.A mechanism involving formation of a β-substituted radical, followed by a simultaneous electron transfer and elimination of the leaving group (reductive elimination) is proposed.