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oai:null:10339/374262026-09-02T14:21:48Zcom_10339_14934col_10339_38132

Elkazaz, Salwa Salah 2012-09-05T08:35:15Z 2013-09-05T08:30:09Z 2012 https://wakespace.lib.wfu.edu/handle/10339/37426 Triplet excited 9,10-anthraquinones can abstract H from alkyl groups ortho to the carbonyl. The hydrogen transfer results in a 1,x biradical which then undergoes a variety of reactions. One of these, oxidation of an alkyl substituent ortho to one of the carbonyls, was believed to go through formation of an endoperoxide. Photolysis of 1-methyl-9,10-anthraquinones using 419 nm light gave the corresponding suggested endoperoxide cleanly, supporting the hypothesis. Reduction of the endoperoxide resulted in oxidation of the ortho methyl group. The scope of the reaction was examined by using the photochemical hydroxylation in the first synthesis of a natural product, 9'-hydroxyaloesaponarin II. en Wake Forest University Anthracene Cancer Photochemistry Photocleavage Singlet Oxygen PHOTOCHEMICAL HYDROXYLATION OF 1-METHYLANTHRAQUINONES: SYNTHESIS OF 9`-HYDROXYALOESAPONARIN II Dissertation Jones, Paul B. Glenn, Anne G. Colyer, Christa L. Welker, Mark E. Alexander, Rebecca Chemistry 2013-09-05 restricted