Formation of a meso-Tetraphenylsecochlorin and a Homoporphyrin with a Twist

The osmium tetroxide-mediated dihydroxylation of meso-tetraphenylporphyrin leads to the formation of the vic-diol meso-tetraphenyl-2,3-vic-diol-2,3-chlorin. The corresponding Ni(II) complex was converted by lead tetraacetate into (meso-tetraphenyl-2,3-secochlorinato-2,3-dialdehyde)nickel(II). This n...

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Bibliographic Details
Published in:Journal of organic chemistry 1998-04, Vol.63 (7), p.2094-2098
Main Authors: Brückner, Christian, Rettig, Steven J., Dolphin, David
Format: Article
Language:English
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Summary:The osmium tetroxide-mediated dihydroxylation of meso-tetraphenylporphyrin leads to the formation of the vic-diol meso-tetraphenyl-2,3-vic-diol-2,3-chlorin. The corresponding Ni(II) complex was converted by lead tetraacetate into (meso-tetraphenyl-2,3-secochlorinato-2,3-dialdehyde)nickel(II). This novel pigment undergoes an almost quantitative, intramolecular double acetal formation when treated with methanol in the presence of acid to produce a porphyrinoid in which one pyrrolic unit is formally replaced by a six-membered ring. An X-ray crystal structure determination, the first for such a homoporphyrin, reveals the severely twisted conformation of its chromophore.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo971156t