Preparation of Phthalide‐Containing Methacrylates.

Puzin, Yu. I.; Chebaeva, T. V.; Galinurova, E. I.; Муслухов, Р. Р.; Monakov, Yu. B.; Сыркин, А. М.

doi:10.1002/chin.200510112

Cited by 5 publications

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“…Isobenzofuranones, often called phthalides, are attractive synthetic targets due to their frequent occurrence in various biologically active natural products They are also key intermediates in the synthesis of a variety of fine chemicals and pharmaceuticals, heat resistant polymers, functionalized anthracenes, naphthalenes and naphthacene‐based natural products …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Isobenzofuranones by Cobalt Catalyzed [2+2+2] Cycloaddition

et al. 2020

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Section: Introductionmentioning

confidence: 99%

Synthesis of Isobenzofuranones by Cobalt Catalyzed [2+2+2] Cycloaddition

et al. 2020

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“…The choice of 3,6-bis(o-carboxybenzoyl)-N-isopropylcarbazole 6 (Scheme 4) exhibiting the properties of tertiary amine has been primarily governed by its effect (stronger than that of metallocenes) on the microstructure of the poly(methyl methacrylate) prepared in its presence: the content of syndio structures is up to 72% in the case of the synthesis at 75°С [56]. However, the polymerization has been substantially decelerated in the case of the compound 6-organic peroxide.…”

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confidence: 99%

Iron compounds in controlled radical polymerization: Ferrocenes, (clathro)chelates, and porphyrins

Islamova

2016

Russ J Gen Chem

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Abstract-Experimental data on the application of metal complexes in radical polymerization of vinyl monomers collected over the recent 15 years have been analyzed and generalized. Special attention has been given to (un)substituted ferrocenes, macrocyclic (clathro)chelates, and iron porphyrinates as well as to the approaches to enhance their catalytic activity in controlled synthesis of macromolecules. The mentioned systems have been compared with each other as well as with selected complexes of other transition metals. It has been shown that the electronic and spatial structures of the metal complexes are related to their efficiency in the radical polymerization reactions. Keywords: controlled radical polymerization, metallocene, (clathro)chelate, metal porphyrinate, catalytic/ initiating system Application of metal complexes opens broad prospects to control the polymerization processe and to prepare polymer materials with improved physicochemical properties. The metal complex catalysis has become of special importance in the field of controlled radical polymerization over the recent 15 years.The term "controlled radical polymerization" is generally referred to "living" or "pseudo-living" radical polymerization; its mechanism, irrespectively of the type of the catalysts/mediators applied (metal complexes [1-11], nitroxyl compounds [12-14], thioesters [15,16], etc.) is based on minimization of the probability of the interaction between the propagating radicals, resulting in the irreversible chain termination. This allows for control of molecular parameters of the prepared polymers, in particular, reduction of the polydispersity coefficient down to M w /M n = 1.1, achieving the linear behavior of the number-average molecular mass (M n ) as function of the conversion, elimination of the undesirable gel effect, and preparation of block copolymers.Atom Transfer Radical Polymerization (ATRP) [1], Transition Metal-Catalyzed Living Radical Polymerization [7], and Organometallic Mediated Radical Polymerization (OMRP) [11] are among the types of controlled radical polymerization. The first approach is based on the use of halides of organic complexes of transition metals, leading to the formation of labile terminal carbon-halogen bond (P n -Hlg). Under certain conditions, this bond is capable of dissociation to regenerate the initial or new active radical further propagating the polymer chain (Scheme 1).Here P n · stands for the propagating macroradical, М is the vinyl monomer, HlgMt x+1 /L is the metal complex halide (with L as the organic ligand), Mt is the transition metal, and k p is the rate constant of the chain propagation.The second of the listed methods uses stable radical organometallic species or diamagnetic transition metal complexes forming the carbon-metal bond P n -Mt as the regulators of the polymer chain growth [11] (Scheme 2).Due to the similarity of these two approaches their simultaneous operation is often assumed [11].Besides "living" radical polymerization, complexand/or coordination-radical polymeri...

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“…The starting materials 3‐bromophthalide ( 7a ) and o ‐benzoylbenzoic acid ( 4 ) required for the synthesis of the derivatives of γ‐keto acids were prepared by the literature methods . The 3‐bromophthalide was found to be a suitable reagent, and its feasibility for the Heck reaction was studied.…”

Section: Resultsmentioning

confidence: 99%

“…After the completion of reaction, the excess thionyl chloride and the solvent were removed by distillation under reduced pressure. Yield 87%, mp 52–55 °C .…”

Section: Methodsmentioning

confidence: 99%

“…Over the past three decades, the Heck reaction has become one of the most fundamental metal‐catalyzed C–C bond forming processes for the synthesis of complex molecules . It has had a huge impact on organic synthesis despite the disadvantages that the overall coupling of the two fragments requires two discrete activation steps: (1) the formation of an aryl or vinyl halide and (2) the union of two reactants with Pd(0) catalyst.…”

Section: Introductionmentioning

confidence: 99%

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A Facile Synthesis of Novel Cyclic Esters of γ‐Keto Acid Derivatives by Heck Coupling Reaction

Shashikumar

Krishnamurthy

Bhojyanaik

2014

Journal of Heterocyclic Chem

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γ‐Keto acids and esters are highly useful compounds in organic synthesis, because a number of five‐membered carbocycles and various other heterocycles can be readily obtained from them. A number of γ‐keto acids derivatives have been synthesized with high yield by Heck coupling reaction with different alkenes using Pd(OAc)2 as catalyst in dioxane solvent. The obtained products were characterized by elemental analysis, IR, proton NMR, and mass spectral studies.

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Preparation of Phthalide‐Containing Methacrylates.

Abstract: Preparation of Phthalide-Containing Methacrylates. -Different unsaturated products are obtained depending on the polarity of the reaction medium. -(PUZIN, Y. I.; CHEBAEVA, T. V.; GALINUROVA, E. I.; MUSLUKHOV, R. R.; MONAKOV, Y. B.; SYRKIN, A. M.; Russ.

Cited by 5 publications

References 1 publication

Synthesis of Isobenzofuranones by Cobalt Catalyzed [2+2+2] Cycloaddition

Synthesis of Isobenzofuranones by Cobalt Catalyzed [2+2+2] Cycloaddition

Iron compounds in controlled radical polymerization: Ferrocenes, (clathro)chelates, and porphyrins

A Facile Synthesis of Novel Cyclic Esters of γ‐Keto Acid Derivatives by Heck Coupling Reaction

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