Pub No:
345
Title:
The Formation of a meso-Tetra-phenyl-secochlorin and a Homoporphyrin with a Twist
Authors:
Bruckner,C., Rettig, S.J., and David Dolphin
Journal:
J. Org. Chem.
Year:
1998
Pages:
63(7), 2094-2098
Abstract:
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

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