The palladium (II) catalyzed vinyl interchange reaction—II

McKeon, James E.; Fitton, P.

doi:10.1016/0040-4020(72)80129-7

Cited by 70 publications

(27 citation statements)

References 3 publications

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“…Four main synthetic pathways have been reported for the chemical modification of an alcohol with a functional vinyl ether: addition onto acetylene,62 phase transfer catalysis based on a Williamson reaction (between an alcoholate and 2‐chloroethyl vinyl ether),63–65 the modification of vinyl acetate in the presence of an iridium complex,66 and transetherification 63,67–72. This latter strategy has been extensively studied in the presence of either mercuric acetate or palladium acetate, especially by Watanabe and Conlon,67 Mc Keon,73 and Boutevin and Youssef 63. This last study even compared the transetherification with the Williamson reaction.…”

Section: Resultsmentioning

confidence: 99%

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Printz¹

2011

Cancer

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The synthesis and characterization of novel poly(CTFE‐g‐oligoEO) graft copolymers [chlorotrifluoroethylene (CTFE) and ethylene oxide (EO)] are presented. First, vinyl ether monomers bearing oligo(EO) were prepared by transetherification of ω‐hydroxyoligo(EO) with ethyl vinyl ether catalyzed by a palladium complex in 70–84% yields. Two vinyl ethers of different molecular weights (three and 10 EO units) were thus obtained. Then, radical copolymerization of the above vinyl ethers with CTFE led to alternating poly(CTFE‐alt‐VE) copolymers that bore oligo(OE) side chains in satisfactory yields (65%). These original poly(CTFE‐g‐oligoEO) graft copolymers were characterized by 1H, 19F, and 13C NMR spectroscopy. Their molecular weights reached 19,000 g mol−1, and their thermal properties were investigated while their glass transition temperatures ranged between −42 and −36 °C. Their thermogravimetric analyses under air showed decomposition temperatures of 270 °C with 10% weight loss (Td,10%). These novel copolymers are of potential interest as polymer electrolytes in lithium ion batteries, showing room temperature conductivities ranging from 4.49 × 10−7 to 1.45 × 10−6 S cm−1 for unplasticized material. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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Section: Resultsmentioning

confidence: 99%

Organizations join forces to confront global cancer crisis

Printz¹

2011

Cancer

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“…ViBu, VDMB, and VDMV were synthesized by a vinyl ester interchange reaction 10 between VAc and the corresponding acids [isobutyric acid (Wako), 2,2-dimethylbutyric acid (Lancaster), and 2,2-dimethylvaleric acid (Lancaster), respectively]. The reaction was catalyzed with diacetato-(1,10-phenanthroline)palladium(II) (Aldrich) and the vinyl esters were distilled twice.…”

Section: Experimental Materialsmentioning

confidence: 99%

Free-radical polymerization of vinyl esters using fluoroalcohols as solvents: Effect of monomer structure on stereochemistry

Yamada

1999

J. Polym. Sci. A Polym. Chem.

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“…They successfully used (L-L) Pd(OAc) 2 catalyst, where L-L stands for 2,2 -bipyridyl or 1,10phenanthroline chelate, for the transfer vinylation of protected monosaccharides. The efficiency of palladium (II) complex in transfer vinylation has been initially described by McKeon and Fitton [25]. To the best of our knowledge, only two other examples of catalyzed transfer vinylation were reported in the literature: vinylation of steroids [22] and synthesis of glycidol vinyl ether [26].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel functional vinyl ethers that bear various groups

Fayad¹,

Malti²,

Améduri³

et al. 2022

Comptes Rendus. Chimie

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The synthesis of new functionalized vinyl ethers (VEs) by transetherification reaction between ethyl vinyl ether (EVE) and different alcohols is presented. An air-stable palladium catalyst generated in situ efficiently catalyzed the reaction leading to various VEs in a single step with good alcohol conversion (50-82%) and good VE yields (up to 75%). The reaction conditions were optimized in terms of the initial EVE/alcohol molar ratio, alcohol concentration, solvent, presence and nature of the ligand, amount of the catalyst, and choice of the metal precursor. All VEs were characterized using 1 H and 13 C NMR spectroscopy.

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The palladium (II) catalyzed vinyl interchange reaction—II

Cited by 70 publications

References 3 publications

Organizations join forces to confront global cancer crisis

Organizations join forces to confront global cancer crisis

Free-radical polymerization of vinyl esters using fluoroalcohols as solvents: Effect of monomer structure on stereochemistry

Synthesis and characterization of novel functional vinyl ethers that bear various groups

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