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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 17
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Original Articles

Oxidative Addition of Dimethyl Malonate to Styrenes Mediated by Cerium(Iv) Ammonium Nitrate: Some Novel Observations

Vijay Nair Organic Chemistry Division, Regional Research Laboratory CSIR, Trivandrum, 695 019, India
,
Jessy Mathew Organic Chemistry Division, Regional Research Laboratory CSIR, Trivandrum, 695 019, India
&
Latha G. Nair Organic Chemistry Division, Regional Research Laboratory CSIR, Trivandrum, 695 019, India
Pages 3053-3064 | Received 04 Dec 1996, Published online: 22 Aug 2006
 
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Abstract

The oxidative addition of dimethyl malonate to ring substituted styrenes leads to the formation of substituted dimethyl (2-oxo-2-phenylethyl) malonate and methyl 2-oxo-5-phenyltetrahydrofuran-3-carboxylate along with small amounts of substituted dimethyl [2-(nitrooxy)-2-phenylethyl] malonate and dimethyl 2-methoxy-2-phenylethyl) malonate. A tentative mechanism which supports the formation of these products is also presented.

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Related Research Data

Relative Rates for the Addition Reactions of the Malonyl Radical to Substituted Styrenes Induced by Cerium(IV) Ammonium Nitrate and Tributyltin Hydride. A Comparison
Source: American Chemical Society (ACS)
Oxidation of diethyl (pyridylmethyl)malonates with manganese(III) acetate, cerium(IV) ammonium nitrate, and iron(III) perchlorate in the presence of alkenes and alkynes
Source: American Chemical Society (ACS)
1,2- And 1,4-addition in the reactions of carbonyl compounds with 1,3-butadiene induced by cerium(IV) ammonium nitrate
Source: American Chemical Society (ACS)
Generation of Cation Radicals from Enamines and Their Reactions with Olefins
Source: The Chemical Society of Japan
Synthesis of Spiroannulated Dihydrofurans by Cerium(IV) Ammonium Nitrate Mediated Addition Of 1,3-Dicarbonyl Compounds to Exocyclic Alkenes
Source: Informa UK Limited
Synthesis of 4-Oxoaldehydes by the Ceric Ammonium Nitrate Promoted Oxidative Addition of Trimethylsilyl Enol Ethers to Ethyl Vinyl Ether
Source: Georg Thieme Verlag KG
Aromatic acetonylation promoted by manganese(III) and cerium(IV) salts
Source: American Chemical Society (ACS)
Synthesis of 3-Acyl and 3-Carboalkoxyfurans by the Ceric Ammonium Nitrate Promoted Addition of 1,3-Dicarbonyl Compounds to Vinylic Acetates
Source: Informa UK Limited
Oxidative cyclization of .delta.,.epsilon.- and .epsilon.,.zeta.-unsaturated enol silyl ethers
Source: American Chemical Society (ACS)
Manganese(III) mediated reactions of unsaturated systems
Source: Georg Thieme Verlag KG
Synthesis of 1,4-dicarbonyl compounds by the ceric ammonium nitrate promoted reaction of ketones with vinyl and isopropenyl acetate
Source: Elsevier BV
Oxidation of organic compounds with cerium(IV). XIV. Formation of a .alpha.-azido-.beta.-nitratoalkanes from olefins, sodium azide, and ceric ammonium nitrate
Source: American Chemical Society (ACS)
Dimethyl arylmalonates from cerium(IV) ammonium nitrate promoted reactions of dimethyl malonate with aromatic compounds in methanol
Source: Elsevier BV
Generation of Cation Radicals from Allylic Sulfides and Their Reactions with Silyl Enol Ethers by the Use of Cerium(IV) Ammonium Nitrate
Source: The Chemical Society of Japan
Synthesis of substituted tetrahydronaphthalenes by manganese(III), cerium(IV), and iron(III) oxidation of substituted diethyl .alpha.-benzylmalonates in the presence of olefins
Source: American Chemical Society (ACS)
Free-radical aromatic nitromethylation promoted by cerium(IV)
Source: American Chemical Society (ACS)
Oxidation by metal salts. X. One-step synthesis of .gamma.-lactones from olefins
Source: American Chemical Society (ACS)
Synthesis of unsymmetrical 1,4-diketones by the ceric ammonium nitrate promoted cross-coupling of trimethylsilyl enol ethers
Source: Elsevier BV
Oxidative addition of 1,3-dicarbonyl compounds to alkenes mediated by cerium(IV) ammonium nitrate and manganese(III) acetate: a comparative study
Source: Royal Society of Chemistry (RSC)
Manganese(III)-based oxidative free-radical reaction of α-allyl-β-keto ester with molecular oxygen
Source: Elsevier BV
Transition Metal-Promoted Free-Radical Reactions in Organic Synthesis: The Formation of Carbon-Carbon Bonds
Source: American Chemical Society (ACS)
Intermolecular Tandem Addition/Esterification Reaction of Alkenes with Malonates Leading to γ‐Lactones Mediated by Molecular Iodine under Visible Light Irradiation
Source: Wiley
Oxidation by metal salts. IX. Formation of cyclic ketones
Source: American Chemical Society (ACS)
Facile synthesis of dihydrofurans by the cerium(IV) ammonium nitrate mediated oxidative addition of 1,3-dicarbonyl compounds to cyclic and acyclic alkenes. Relative superiority over the manganese(III) acetate mediated process
Source: Royal Society of Chemistry (RSC)
Redox induced radical and radical ionic carbon-carbon bond forming reactions
Source: Elsevier BV
Cerium(IV) ammonium nitrate mediated addition of dimethyl malonate to styrene: a remarkable reaction
Source: Royal Society of Chemistry (RSC)
Diarryl-a-heteroarylmalonates from Cerium(IV)-promoted Reactions of Dialkyl Malonates with Heterocyclic Compounds
Source: The Japan Institute of Heterocyclic Chemistry
Identification and Kinetic Study of the Peroxymalonyl Radical in the Aerobic Oxidation of Malonic Acid by Cerium(IV)
Source: American Chemical Society (ACS)

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