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Volumn , Issue 6, 2009, Pages 945-948

Meso-oxidation of porphyrins: Convenient iron(III)-mediated synthesis of dioxoporphyrins

Author keywords

Dioxoporphyrin; FeCl3 6H2O; Oxidation

Indexed keywords

FERRIC ION; PORPHYRIN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS;

EID: 63849269477 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1088212 Document Type: Article

Times cited : (13)

References (14)

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12
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- Typical Procedure for the Fe(III)-Mediated Synthesis of Dioxoporphyrins Zn2 A mixture of Znla (100 mg, 0.19 mmol, 1.0 equiv) and FeCl36H2O (513 mg, 10 equiv) was stirred in DMF (20 mL) in air at 130 °C for 5 h. After cooling to r.t, the reaction mixture was diluted with CH2Cl2 (20 mL) and washed with H 2O three times. The organic layer was passed through dry SiO 2 and evaporated to dryness. The resulting solid was crystallized from CH2Cl2-MeOH or purified by flash column chromatography (SiO2, 300-400 mesh, PE-EtOAC 4:1) to produce the desired dioxoporphyrin Zn2a (90 mg, 85% yield, Characterization Data for Selected Representative Compounds Dioxoporphyrin Zn2a 1H NMR (300 MHz, acetone-d6, δ, 6.28-6.31 (m, 4 H, β-H, 6.87-6.90 (m, 4 H, β-H, 7.33 (d, J=3.6 Hz, 4 H, PhH, 7.40-7.42 (m, 6 H, PhH, MS MALDI
- 2) was 0.0465 (all data). CCDC 711638 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.

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