OXIDATION OF METHOXYBENZENES TO P-BENZOQUINONES CATALYZED BY METHYLTRIOXORHENIUM(VII)

被引:69
作者
ADAM, W [1 ]
HERRMANN, WA [1 ]
SAHAMOLLER, CR [1 ]
SHIMIZU, M [1 ]
机构
[1] TECH UNIV MUNICH,INST ANORGAN CHEM,D-85747 GARCHING,GERMANY
关键词
ARENE OXIDE; P-BENZOQUINONE; HYDROGEN PEROXIDE; METHYLTRIOXORHENIUM; OXIDATION; PEROXO COMPLEX;
D O I
10.1016/1381-1169(94)00070-0
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Methoxy-substituted benzenes 1 are oxidized with aqueous hydrogen peroxide catalyzed by methyltrioxorhenium(VII) in acetic acid to yield the p-benzoquinones 3 in moderate yields. An intermediary diperoxo rhenium(VII) complex rather than peracetic acid is the dominating oxidizing species, since oxidation also proceeds in ethanol under peracid-free conditions. Acid played an important role, especially in the oxidation of p-methoxyphenols 2 to p-benzoquinones 3. An arene oxide mechanism is postulated for the formation of p-benzoquinones, which would account for the participation of the acid and also overoxidation by cleavage of the arene oxide ring with hydrogen peroxide.
引用
收藏
页码:15 / 20
页数:6
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