CHED 839 |
Photochemical rearrangements of 1-hydroxy and alkoxyanthraquinones
| Paul B. Jones, Sarah C. Hubbard, Robert G. Brinson, and John D. Reynolds. Department of Chemistry, Wake Forest University, 1834 Wake Forest Road, Salem Hall, Winston-Salem, NC 27109 |
| Blankespoor has thoroughly investigated the photochemistry of 1-alkoxyanthraquinones. The usual intramolecular reaction involves an electron transfer and subsequent hydrolysis producing 1-hydroxyanthraquinone and the corresponding aldehyde. We were interested in investigating this reaction when the alkyl group is such that an alpha,beta-unsaturated aldehyde would be produced. During the investigation, we discovered several noteworthy rearrangements. One example is shown below. The relative yield of hydroxyanthraquinone, aldehyde, and rearranged products is dependent on solvent, concentration, and oxygen concentration. We will present the results of our investigation, as well as a mechanistic discussion and possible biological implications of the reaction.  |
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