ORGN 700 |
| 1,8-Anthraquinone-18-crown-5 is similar in size to 18-crown-6 except for the incorporation of an intraannular carbonyl group from the anthraquinone which is integrated into the cyclic polyether ring. Since the anthraquinone is substituted only on one side by the polyether chain, the anthraquinone is asymmetric and the two carbonyl groups may exhibit different reduction chemistry. Unlike other quinones, anthraquinone can be partially reduced to the anthrone, where in this case we have observed that the intraannular carbonyl has been reduced and the resulting anthrone/anthonol tautomerization chemistry investigated. Using different reducing agents we have also isolated both 10-hydroxy-10-hydroanthracene-9-one and 9,10-dihydroxy-9,10-dihydroanthracene species, as well as a new dimer that contains two crown rings formed by the oxidation of 10-hydroxy-10-hydroanthracene-9-one. Stereochemistry has been confirmed by single-crystal X-ray crystallography in each case. The luminescence chemistry of these different reduced anthraquinone species are also presented regarding the detection of metal ions of clinical and environmental importance. |
|
Asymmetric Reactions, Combinatorial Chemistry, Molecular Recognition and Self-Assembly, Proteins, Peptides, Amino Acids and Enzyme Inhibitors
8:00 PM-10:00 PM, Wednesday, March 28, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |