50827-56-0Relevant academic research and scientific papers
Biomimetic oxidation of veratryl alcohol with H2O2 catalyzed by iron(III) porphyrins and horseradish peroxidase in ionic liquid
Kumar, Anil,Jain, Nidhi,Chauhan
, p. 411 - 414 (2008/01/06)
3,4-Dimethoxybenzyl alcohol (veratryl alcohol) is a model compound for lignin substructures and its oxidation with H2O2 catalyzed by iron(III) porphyrins and horseradish peroxidase (HRP) in ionic liquids has been described. Veratraldehyde and 2-hydroxymethyl-5-methoxy-2,5-cyclohexadiene- 1,4-dione were the two major products of the oxidation of veratryl alcohol at room temperature. The iron(III) porphyrin or HRP immobilized in ionic liquids showed increased catalytic activity and can be recycled and this is believed due to the stabilization of highvalent oxoiron(IV) π-cation radical intermediate generated in the reaction. Georg Thieme Verlag Stuttgart.
Preparation, catalytic activity of supported metalloporphyrin catalysts on polyvinylpyridine polymers and related molecular modelling studies (case of a proximal ligand provided by the polymer itself)
Pattou, Denis,Labat, Gilles,Defrance, Sabine,Seris, Jean-Louis,Meunier, Bernard
, p. 78 - 88 (2007/10/02)
Anionic manganese and iron porphyrin complexes derived from sulfonated TPP, TMP or TDCPP ligands can be easily attached to a poly(4-vinylpyridinium) polymer.First the metalloporphyrin is linked to the neutral poly(4-vinylpyridine) by a pyridine from the polymer itself, which acts as a proximal ligand.The protonation of the other pyridine residues then reinforces the linkage of metalloporphyrins by additional strong electrostatic interactions (molecular modelling studies confirm this hypothesis).Such supported metallophorphyrins with a proximal ligand arising from the polymer can be used in the potassium monopersulfate oxidation of lignin model molecules in the absence of an excess of free pyridine, which is usually required for efficient manganese porphyrin-catalyzed reactions. supported catalysts / metalloporphyrins / poly(vinylpyridine) / proximal effect
Iron Porphyrin-Catalyzed Oxidation of 1,2-Dimethoxyarenes: A Discussion of the Different Reactions Involved and the Competition between the Formation of Methoxyquinones or Muconic Dimethyl Esters
Artaud, Isabelle,Ben-Aziza, Khaled,Mansuy, Daniel
, p. 3373 - 3380 (2007/10/02)
This paper describes the oxidation of an α,β-diarylpropane lignin dimer model and other dimethoxyarenes by several iron porphyrin-based biomimetic systems.From 1-(3,4-dimethoxyphenyl)-2-phenylpropanol (1), three types of products are identified: the 3,4-dimethoxybenzaldehyde derived from the Cα-Cβ cleavage of the propyl side chain and either quinones or muconic dimethyl esters resulting from oxidations at level of the dimethoxyaryl group.The selectivity of the reaction is discussed with respect to the nature and reactivity of the high-valent iron-oxo species formed upon reaction of the oxidants, H2O2 or magnesium monoperoxyphthalate (MMP), with the iron porphyrins.Fe(TF5PP)Cl-catalyzed oxidation of 1 by H2O2 in an aprotic medium (CH3CN/CH2Cl2), yields a clean "lignin peroxidase-like" reaction with selective formation of the aldehyde.In an aqueous buffered solution, MMP oxidation of para-substituted 1,2-dimethoxyarenes catalyzed by an iron tetrakis(pentafluorophenyl)-β-tetrasulfonatoporphyrin, Fe(TF5PS4P), clearly depends on the electronic properties of the para-substituent.The reaction is selective for para-quinone formation in the case of an electron-releasing group and for muconic dimethyl ester formation in the case of an electron-withdrawing group.
Iron porphyrin catalyzed oxidation of lignin model compounds: the oxidation of veratryl alcohol and veratryl acetate
Cui, Futong,Dolphin, David
, p. 2314 - 2318 (2007/10/02)
meso-Tetra(2,6-dichloro-3-sulfonatophenyl)porphyrin iron chloride catalyzes the oxidation of 3,4-dimethoxybenzyl alcohol (veratryl alcohol) in aqueous solution to give veratraldehyde along with demethoxylation and ring-cleavage products.The isolation of a direct ring-cleavage product from the oxidation of veratryl acetate in aqueous solution supports the previously proposed ring-cleavage mechanisms.The oxidation in methanol, however, does not lead to ring-cleavage products.When veratryl alcohol was oxidized in methanol, solvent was found to be incorporated into the 3-position of veratryl alcohol, giving new insight into the mechanism of oxidation.
A New Easy Access to Quinones from Iron Porphyrin-catalysed Oxidation of Methoxyarenes by Magnesium Monoperoxyphthalate
Artaud, Isabelle,Aziza, Khaled Ben,Chopard, Claude,Mansuy, Daniel
, p. 31 - 33 (2007/10/02)
Electron-rich methoxyarenes were oxidized with high yields (55-100percent) and under mild conditions to the corresponding paraquinones by magnesium monoperoxyphthalate in the presence of catalytic amounts of a water-soluble iron porphyrin; the reaction was used to prepare methoxatin.
Factors Controlling the Reactivity of a Ligninase Model Based on the Association of Potassium Monopersulfate to Manganese and Iron Porphyrin Complexes
Labat, Gilles,Meunier, Bernard
, p. 5008 - 5011 (2007/10/02)
An efficient ligninase model based on the association of potassium monopersulfate to iron and manganese porphyrin in solution or immobilized onto an ion-exchange resin is reported.High catalytic conversion of veratryl alcohol or 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol, a useful model molecule for checking the ability of cleaving Cα-Cβ bonds of arylglycerol-β-aryl ether linkages existing in lignin itself, is obtained at room temperature in a single-phase solution (buffered water/acetonitrile, 75/25, v/v) at pH 2-3 for iron porphyrin or at pH 4.5-6.0 for manganese porphyrin.The porphyrin ligand used in the present study is the meso-tetrakis(p-sulfonatophenyl)porphyrin (TPPS).Catalytic activities can be as high as eight cycles per second.
