Regiospecific beta-functionalization of free-base porphyrins by pseudohalogens.

Regiospecific beta-functionalization of free-base porphyrins by pseudohalogens. Research Abstract Details 

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Regiospecific beta-functionalization of free-base porphyrins by pseudohalogens. Abstract Text:

Wei Zhang,Matthew N Wicks,Paul L Burn,Wei Zhang,Matthew N Wicks,Paul L Burn,

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.

Regiospecific beta-functionalization of free-base porphyrins by pseudohalogens. Publishing Authors By Initials

W Zhang,MN Wicks,PL Burn,W Zhang,MN Wicks,PL Burn,

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Regiospecific beta-functionalization of free-base porphyrins by pseudohalogens. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Organic & biomolecular chemistry

VOLUME: 6

Page Numbers: 879-86

Journal Abbreviation: Org. Biomol. Chem.

ISSN: 1477-0520

DAY: 1

MONTH: 02

YEAR: 2008

Regiospecific beta-functionalization of free-base porphyrins by pseudohalogens. Information

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LANGUAGE: eng

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Grant and Affiliation Information for Regiospecific beta-functionalization of free-base porphyrins by pseudohalogens.

AFFILIATION: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UKOX1 3TA.

Country: England

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MEDLINETA: Org Biomol Chem

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