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PHOTOCHEMICAL HYDROXYLATION OF 1-METHYLANTHRAQUINONES: SYNTHESIS OF 9`-HYDROXYALOESAPONARIN II

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abstract
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.
subject
Anthracene
Cancer
Photochemistry
Photocleavage
Singlet Oxygen
contributor
Elkazaz, Salwa Salah (author)
Jones, Paul B. (committee chair)
Glenn, Anne G. (committee member)
Colyer, Christa L. (committee member)
Welker, Mark E. (committee member)
Alexander, Rebecca (committee member)
date
2012-09-05T08:35:15Z (accessioned)
2013-09-05T08:30:09Z (available)
2012 (issued)
degree
Chemistry (discipline)
embargo
2013-09-05 (terms)
identifier
http://hdl.handle.net/10339/37426 (uri)
language
en (iso)
publisher
Wake Forest University
title
PHOTOCHEMICAL HYDROXYLATION OF 1-METHYLANTHRAQUINONES: SYNTHESIS OF 9`-HYDROXYALOESAPONARIN II
type
Dissertation

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