Porphyrin誘導体の合成

概要

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The reaction between pyrrole and a carbonyl compound gave porphyrinogen (12) and porphyrin (15) which had substituents on the positions of meso (5,lO, 15,20). The reaction was composed of successive reactions from chain dimer to trimer, then to tetramer, and then to ring tetramer. In the case of pyrrole and ketones (acetone, cyclohexanone and methyl ethyl ketone), porphyrinogenes (12a, b, c) were easily prepared and chain dimer was also prepared as by-product. In the case of benzophenone which had a big stereo obstruction, the reaction stopped at the stage of chain dimer (11d). In the case of pyrrole and benzaldehyde, porphyrinogen (14a) was easily yielded. The compound (14a) was dehydrogenated by autooxidation, yielding porphyrin (15a). On the other hand, in the case of other aldehydes (acetaldehyde and formaldehyde), the reaction stopped at the stage of dimer and trimer. These results show the tendency of reversion of the order of chemical reactivity of ketone and aldehyde. These results must be explained that ring compound which has suitable substituents on meso (5,10,l5,20) positions of porphyrin can be prepared because of its stereo chemical and thermodynamical stability.
東海大学の論文