Highly strained dihydroanthraquinones: oxidation versus elimination

Graphic 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...

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Bibliographic Details
Published inTetrahedron letters Vol. 45; no. 14; pp. 2955 - 2959
Main Authors Reynolds, John D, Brinson, Robert G, Day, Cynthia S, Jones, Paul B
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.03.2004
Elsevier
Subjects
Anthraquinone
Chemistry
Chemistry, Organic
Oxidation
Physical Sciences
Science & Technology
Strain
Oxidation
Anthraquinone
Strain
strain
ACID-DERIVATIVES
anthraquinone
RESONANCE
DIELS-ALDER REACTION
ISOMERIZATION
SUBSTITUENTS
oxidation
PHOTOCHEMISTRY
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Summary:Graphic 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 acetate substitution dehydrogenated as expected. Furthermore, oxidation of the cyclohexadiene ring using iodine failed due to a competitive iodolactonization reaction. The desired strained anthraquinones could be prepared, in low yield, by treatment of the resulting lactones with acidic ethanol.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.02.041