MECHANISTIC INVESTIGATION OF THE ACENAPHTHENEQUINONE SENSITIZED BARTLETT PHOTO-EPOXIDATION OF OLEFINS - CONCOMITANT OXIDATION OF THE SENSITIZER

被引：22

作者：

KOO, JY ^{[1
]}

SCHUSTER, GB ^{[1
]}

机构：

[1] UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 05期

关键词：

D O I：

10.1021/jo01319a041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photolysis of acenaphthenequinone in CH2CI2solution continuously saturated with oxygen generates 1, 8-naphthalic anhydride in 80% isolated yield. When an olefin is included in the reaction solution it is converted to a mixture of oxidizedproducts consisting mainly of allylic hydroperoxide and epoxide. It is demonstrated that the quantum efficiency for quinone oxidation is independent of quinone and olefin concentration. A mechanism is suggested for which an initial reaction between excited quinone and oxygen results in covalent bond formation. Subsequent rearrangement of this intermediate accounts for the results observed. © 1979, American Chemical Society. All rights reserved.

引用

页码：847 / 851

页数：5

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