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Oxidation of methoxybenzenes to p-benzoquinones catalyzed by methyltrioxorhenium(VII)

✍ Scribed by Waldemar Adam; Wolfgang A. Herrmann; Chantu R. Saha-Möller; Masao Shimizu

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
529 KB
Volume
97
Category
Article
ISSN
1381-1169

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✦ Synopsis

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(W) 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 ofp-benzoquinones, which would account for the participation of the acid and also overoxidation by cleavage of the arene oxide ring with hydrogen peroxide.

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