Issue 5, 2008
From the journal:

Organic & Biomolecular Chemistry

Regiospecific β-functionalization of free-base porphyrins by pseudohalogens

Wei Zhang,a   Matthew N. Wicksa  and  Paul L. Burn*b  

* Corresponding authors

a Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UK

b Centre for Organic Photonics and Electronics, School of Molecular and Microbial Sciences, University of Queensland, Chemistry Building, Queensland, Australia

Abstract

Pseudohalogens based on iodine (‘I–X’) can be used to regiospecifically introduce chlorine atoms or acetoxy groups onto the β-positions of meso-tetraphenylporphyrins (TPPs). TPPs and a quinoxaline derivative were reacted with iodine monochloride to give mono- or di-chlorinated porphyrins, such that when two chlorine atoms were added they were placed antipodally on the porphyrin ring. Reaction of the porphyrins with a mixture of iodine and silver acetate gave the corresponding mono- and di-acetoxylated porphyrins. The acetoxylated porphyrins could be simply transformed to the corresponding hydroxyporphyrins with subsequent oxidation with the Dess–Martin periodinane, giving a simple new route to chlorin-α-diones and bacteriochlorin-tetraones. From the products of the reactions and a UV–visible spectroscopic study, it is proposed that the reactions proceed via a single electron transfer mechanism through a porphyrin cation radical intermediate.

Graphical abstract: Regiospecific β-functionalization of free-base porphyrins by pseudohalogens

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/B718542A
Article type
Paper
Submitted
30 Nov 2007
Accepted
19 Dec 2007
First published
01 Feb 2008

Org. Biomol. Chem., 2008,6, 879-886

Permissions

Request permissions

Regiospecific β-functionalization of free-base porphyrins by pseudohalogens

W. Zhang, M. N. Wicks and P. L. Burn, Org. Biomol. Chem., 2008, 6, 879 DOI: 10.1039/B718542A

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.

Social activity

Spotlight

Advertisements