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Solid state redox chemistry of hydroquinones and quinones

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
49
Issue
1
Identifiers
DOI: 10.1016/s0040-4020(01)80510-x

Abstract

Abstract Solid state ceric ammonium nitrate (CAN) oxidation of hydroquinones to the corresponding quinones, gives best results when operating with ultrasonic irradiation. Nitrogen dioxide plays a key role in these “solid-solid” oxidations. The oxidation of hydroquinones to quinones can also be achieved in a unique “solid-solid-solid” reaction, i.e., by using a limited amount of CAN in the presence of a full equivalent of a solid cooxidant such as KBrO 3. Reduction of quinones with sodium dithionite in the solid state gives rise to the corresponding highly colored quinhydrones and, eventually, to hydroquinones.

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