Bulletin of the Chemical Society of Japan p. 3464 - 3470 (1983)
Update date:2022-08-04
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Sawaki
The photooxidation of phenanthrenequinone (PhQ) under oxygen afforded diphenic acid and its peroxy acid, while acenaphthenequinone (AcQ) predominantly yielded 1,8-naphthalenedicarboxylic anhydride. The photolysis of PhQ or AcQ in the presence of olefins afforded predominantly 1:1 cycloadducts and the photoepoxidation was a very minor one accompanying significant amount of C-C clevage of olefins. These results show that the photoreaction of PhQ or AcQ with olefins is very fast and competitive with the quenching and/or reaction with oxygen. The photoepoxidation of stilbene in the presence of dimethyl sulfoxide resulted in a high selectivity ( greater than 98%) for the trans-epoxide.
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Doi:10.1016/S0040-4039(00)71489-4
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(1982)
