Issue 0, 1967

Pyrroles and related compounds. Part XII. Stepwise synthesis of porphyrins through a-oxo-bilanes

Abstract

Stable crystalline dibenzyl a-oxobilane-1′,8′-dicarboxylates have been prepared from 5-benzyloxycarbonyl-5′-chloromethylpyrroketones and 5′-benzyloxycarbonylpyrromethane-5-carboxylic acids. The internuclear carbonyl group can be removed by reduction with diborane, and then hydrogenolysis of the benzyloxycarbonyl groups and dehydrogenation with t-butyl hypochlorite leads to b-bilene-1′,8′-dicarboxylic acids, which are cyclised with methyl orthoformate and trichloroacetic acid and aerially oxidised to porphyrins. The examples of mesoporphyrin IX dimethyl ester, 4-ethyl-6,7-dimethoxycarbonylethyl-1,2,3,5,8-pentamethyl-porphin, and 2-ethyl-6,7-dimethoxycarbonylethyl-1,3,4,5,8-pentamethyl-porphin demonstrate that the synthesis is rational.

Article information

Article type
Paper

J. Chem. Soc. C, 1967, 2045-2059

Pyrroles and related compounds. Part XII. Stepwise synthesis of porphyrins through a-oxo-bilanes

A. H. Jackson, G. W. Kenner and G. S. Sach, J. Chem. Soc. C, 1967, 2045 DOI: 10.1039/J39670002045

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements