The Journal of Organic Chemistry

Lithium aluminum hydride reduction of peri-alkoxy-9, 10-anthraquinones

N Shyamasundar, P Caluwe

Index: Shyamasundar, Nagaraj; Caluwe, Paul Journal of Organic Chemistry, 1981 , vol. 46, # 8 p. 1552 - 1557

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Citation Number: 14

Abstract

The outcome of LiAlH4 reduction of 9, lO-anthraquinones is greatly influenced by electronegative substituents in positions peri to the carbonyl groups of the quinone. Reductions of 1, 4, 1, 5-, and l, &dimethoxyanthraquinones proceed to the anthrone stage. The critical role of the peri-methoxy group is evident from the comparison with the reduction of 2, 6-dimethoxyanthraquinone and the parent anthraquinone, which give dihydro diols ...

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