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Trapping a labile adduct formed between an ortho-quinone methide and 2'-deoxycytidine

Michael P McCrane1, Emily E Weinert, Ying Lin

  • 1Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.

Organic Letters
|February 11, 2011
PubMed

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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...