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28.9.1.1.1.3 Variation 3: Using Silver(I) Oxide

DOI: 10.1055/sos-SD-028-00642

Carreño, M. C.; Ribagorda, M.Science of Synthesis, (200628638.

Generally, oxidations mediated by silver(I) oxide require mild reaction conditions; therefore, no special precautions need be considered. Typical solvents such as acetone, diethyl ether, benzene, or toluene are used. No additives are generally required to perform the reaction, normally at room temperature or under reflux, but magnesium sulfate is used in some cases. Usually, the starting aminophenols or benzenediamines have N-alkyl, N-aryl, or N-sulfonylaryl groups, to stabilize the final benzoquinone imines and diimines. This procedure has been frequently employed to synthesize benzo-1,4-quinone mono- and diimines, with satisfactory conversions and yields.

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