Tetrahedron

A novel acid-catalyzed rearrangement of 9, 10-diaryl-9, 10-dihydroanthracene-9, 10-diols affording 10, 10′-diaryl-9-anthrones

M Smet, J Van Dijk, W Dehaen

文献索引：Smet, Mario; Van Dijk, Joachim; Dehaen, Wim Tetrahedron, 1999 , vol. 55, # 25 p. 7859 - 7874

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被引用次数: 25

摘要

Usually, 9, 10-diarylanthracenes can be obtained by reduction of the corresponding 9, 10- diaryl-9, 10-dihydroanthracene-9, 10-diols with KI/NaH2PO2 in acetic acid. In contrast, we found that in case of heteroaromatic aryl substituents and when peri substituents are present on the anthracene residue, high amounts of anthrones are formed. These anthrones can be considered to result from a vinylogous pinacol rearrangement of the initial diol. To the best ...