Tetrahedron letters

Highly strained dihydroanthraquinones: oxidation versus elimination

JD Reynolds, RG Brinson, CS Day, PB Jones

Index: Reynolds, John D.; Brinson, Robert G.; Day, Cynthia S.; Jones, Paul B. Tetrahedron Letters, 2004 , vol. 45, # 14 p. 2955 - 2959

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Citation Number: 2

Abstract

The chemistry of strained dihydroanthraquinones was investigated for the purpose of developing syntheses for highly strained anthraquinones. The reaction of (1, 4-dihydro-9, 10- dioxo-anthracen-1-yl)-acetates with triethylamine under aerobic conditions was found to be dependent on the degree of substitution on the acetate. Dihydroanthraquinones bearing dimethylacetates underwent elimination of enolate exclusively, while those without ...