Proceedings of the Symposium on Progress in Organic Reactions and Syntheses
32nd Symposium on Progress in Organic Reactions and Syntheses
Session ID : 2P09
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Synthesis and Structure of Oxidized Porphyrins
*Yusuke HirataMegumi KodamaYohsuke Yamamoto
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Keywords: porphyrin, 16pi, oxidation
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Abstract
When we tried to synthesize sulfur porphyrin by the reaction of OETPPLi2 with SOCl2, a novel oxidized octaethyltetraphenylporphyrin (OETPP) was obtained. The precise X-ray analysis of the oxidized porphyrine by Prof. Iwasaki and Dr. Hashizume revealed the absence of N-H hydrogens, and the porphyrin was much more ruffled when compared with OETPPH2. And OETPP was stabilized partly by CH-pi interaction with CH2Cl2. In addition, the oxidized porphyrin showed a very clear bond altenation. These results clearly showed that it should be the first characterized 16pi non-aromatic porphyrin. Since OETPP is unstable, sterically more congested new octaisobutyltetraphenylporphyrin (OiBTPPH2) was synthesized. As expected, OiBTPP was more stable than OETPP. Synthesis of the sterically more congested new octaisopropyltetraphenylporphyrin(OiPTPPH2) and the oxidized OiPTPP are in progress.
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© 2006 The Pharmaceutical Society of Japan
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