Oxygenation of Aromatic Vinyl Ethers. A Noticeable Formation of Epoxides and Reaction Mechanism

Article abstract of DOI:10.1246/bcsj.54.2330

cis-β-Alkoxystyrenes such as cis-β-methoxy-, cis-β-ethoxy-, and cis-β-isopropoxystyrene were autoxidized as neat at room temperature in the dark even in the absence of any radical generator.UV-irradiation and the use of a radical generator facilitated the oxygenation of these olefins.These oxidations afforded the corresponding epoxides or their derivatives in considerable yields as well as carbonyl compounds resulting from oxidative cleavage of the double bonds.The mechanisms for these oxidations are proposed to involve free-radical chain pathways and charge-transfer complexes between the olefins and oxygen play an important role in the initiation steps.