Title | Formation of a meso-tetraphenylsecochlorin and a homoporphyrin with a twist |
Publication Type | Journal Article |
Year of Publication | 1998 |
Authors | Bruckner, C, Rettig, SJ, Dolphin, D |
Journal | Journal of Organic Chemistry |
Volume | 63 |
Pagination | 2094-2098 |
Date Published | Apr |
Type of Article | Article |
ISBN Number | 0022-3263 |
Keywords | beta, CHLOROPHIN, HYDROPORPHYRINS, OXIDATION, PORPHYRIN ANALOG, SYSTEM |
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. |
URL | <Go to ISI>://000073136500012 |