The Journal of Organic Chemistry

Mechanism of photoepoxidation of olefins with. alpha.-diketones and oxygen

Y Sawaki, CS Foote

Index: Sawaki, Yasuhiko; Foote, Christopher S. Journal of Organic Chemistry, 1983 , vol. 48, # 25 p. 4934 - 4940

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Citation Number: 29

Abstract

The benzil-and biacetyl-sensitized photoepoxidation of olefins in the presence of oxygen has been studied. The photolytic loss of diketone is not affected by the presence of olefins; the ratio of epoxide formation to diketone consumption is in the range of 1-3. An 180-tracer study shows that the epoxide oxygen derives from molecular oxygen and that the recovered oxygen does not scramble. The photoepoxidation is accompanied by CC bond cleavage; ...