Regiospecific β-functionalization of free-base porphyrins by pseudohalogens

Zhang, W., Wicks, M.N. and Burn, P.L. (2008) Regiospecific β-functionalization of free-base porphyrins by pseudohalogens. Organic & Biomolecular Chemistry, 6 5: 879-886. doi:10.1039/b718542a

Author Zhang, W.
Wicks, M.N.
Burn, P.L.
Title Regiospecific β-functionalization of free-base porphyrins by pseudohalogens
Formatted title
Regiospecific β-functionalization of free-base porphyrins by pseudohalogens
Journal name Organic & Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
Publication date 2008-02-01
Year available 2008
Sub-type Article (original research)
DOI 10.1039/b718542a
Open Access Status Not Open Access
Volume 6
Issue 5
Start page 879
End page 886
Total pages 8
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Language eng
Abstract Pseudohalogens based on iodine ('I-X') can be used to regiospecifically introduce chlorine atoms or acetoxy groups onto the beta-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-alpha-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.
Keyword Chemistry, Organic
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: 2009 Higher Education Research Data Collection
School of Chemistry and Molecular Biosciences
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Citation counts: TR Web of Science Citation Count  Cited 9 times in Thomson Reuters Web of Science Article | Citations
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Created: Mon, 09 Mar 2009, 20:52:30 EST by Jennifer Falknau on behalf of School of Chemistry & Molecular Biosciences