Formation of a meso-tetraphenylsecochlorin and a homoporphyrin with a twist

被引：108

作者：

Brückner, C ^{[1
]}

Rettig, SJ ^{[1
]}

Dolphin, D ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 07期

关键词：

D O I：

10.1021/jo971156t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2094 / 2098

页数：5

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