Photochemical Hydroxylation of 1-Methyl-9, 10-anthraquinones: Synthesis of 9′-Hydroxyaloesaponarin II

S Elkazaz, PB Jones

Index: Elkazaz, Salwa; Jones, Paul B. Journal of Organic Chemistry, 2010 , vol. 75, # 2 p. 412 - 416

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Citation Number: 5

Abstract

Photolysis of 1-methyl-9, 10-anthraquinones in the presence of oxygen yields endoperoxides that can be reduced to produce 1-hydroxymethyl-9, 10-anthraquinones. The reaction proceeds in a fashion similar to that of other o-alkylphenones which yield either a 1, 4-diradical or a “photoenol” upon irradiation. Anthraquinones undergo photochemistry at a wavelength where the endoperoxide is transparent, allowing its isolation. A singlet oxygen ...