76036-60-7Relevant academic research and scientific papers
MECHANISM OF THE PHOTOOXIDATION OF AND PHOTOEPOXIDATION WITH CYCLIC alpha -DIKETONES.
Sawaki
, p. 3464 - 3470 (1983)
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.
Keto Oxetanes Produced from Photocycloaddition of o-Quinone and Their Thermolysis. Reaction of 9,10-Phenanthrenequinone with Internally Highly Strained Cyclic Olefins
Maruyama, Kazuhiro,Muraoka, Masami,Naruta, Yoshinori
, p. 983 - 989 (2007/10/02)
The photocycloaddition reaction of 9,10-phenanthrenequinone (PQ) with alicyclic (1a-e) and bicyclic olefins (1f-l) was examined upon irradiation with visible light (>420 nm).Alicyclic olefins gave three kinds of products, keto oxetanes (2), dihydrodioxines (3), and 4, while bicyclic olefins exclusively gave keto oxetanes in fair to high yields (21-90percent).These marked differences were elucidated in terms of the s character of intermediary biradicals.Thermolysis of the five keto oxetanes obtained (2a,d,g,i,l) was examined in basic media and occurred in two different fashions (paths A and B in Scheme I).Correlation between the bond strength of the oxetane ring and the structure of intermediary biradicals is discussed.
