Item Details

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