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Abstract We recently required substantial quantities of 5,8-disubstituted naphthoquinone IV as a precursor for the synthesis of a cyclophane. The sequence chosen to provide the necessary intermediate (IV) utilized a Diels-Alder reaction, between I and p-benzo-quinone, followed by aromatization. Several attempts however at dehydrogenating adduct II (Br2;2 air;3 DDQ or chloranil4) failed, or afforded poor conversions (10–25%). During our research, a report appeared describing the use of commercial grade MnO2in the oxidation of hydroquinones to quinones. 5 Encouraged by the results described in the publication we attempted the oxidation of II with MnO2. When adduct II was stirred in benzene with ordinary MRO2
Mashraqui et al. (Fri,) studied this question.