ORGN 546 |
| Acid catalyzed condensation followed by oxidation (two-step, one-flask method) of 5-pentafluorophenyldipyrromethane with a 5,5-dimethyldipyrromethanedicarbinol species bearing pentafluorophenyl substituents was investigated. The target compound is a phlorin macrocycle possessing electron-withdrawing substituents. Phlorin is an analog of porphyrin that has an sp3 hybridized carbon atom at one of the four bridging meso-positions. The current work complements our ongoing efforts to prepare stable phlorins via the judicious selection of peripheral meso-substituents. The required dipyrromethane and diacyldipyrromethane building blocks were prepared. A systematic examination of acid catalysts, acid concentration, condensation time, and oxidation conditions on the reaction of the dipyrromethane and dipyrromethanedicarbinol was performed via analytical scale reactions monitored by HPLC.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |