Enhanced Spin-capturing Polymerization and Radical Coupling Mediated by Cyclic Nitrones

Ranieri, Kayte; Conradi, Matthias; Chavant, Pierre Y.; Blandin, Véronique; Barner‐Kowollik, Christopher; Junkers, Thomas

doi:10.1071/ch12182

Cited by 14 publications

(9 citation statements)

References 22 publications

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“…While trans diastereoisomers are undoubtedly formed via an exo approach (the less congested) to the E nitrone (the more reactive), [21] the cis diastereoisomers can result from either an exo approach to the Z nitrone or an endo approach to the E nitrone (or from both) In order to control the cis/trans selectivity, 1,3-dipolar cycloaddition was performed with the configurationally stable cyclic nitrone 4. [28] The latter was prepared in three steps from methyl glycinate in 70 % overall yield (See supporting information). Heating of the cyclic nitrone with -C-vinylgalactoside 1b in toluene at 110°C for 70 hours led to two cycloadducts 5 in 54 % yield in a 2:1 ratio (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Constrained C‐Glycosyl Amino Acid Derivatives Involving 1,3‐Dipolar Cycloaddition of Cyclic Nitrone as Key Step

et al. 2020

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An efficient two‐step strategy for the synthesis of constrained C‐glycosyl amino acid derivatives from C‐vinylglycosides involving a 1,3‐dipolar cycloaddition using l‐(–)‐menthone‐derived nitrone as the key step is described. After optimization of 1,3‐dipolar cycloaddition conditions, various C‐vinylglycosides were tested leading exclusively to one diastereoisomer of the corresponding cycloadduct in good to excellent yields. The total facial selectivity observed was also studied by DFT calculations. Original conformationally restricted C‐glycosyl amino acid derivatives (8 examples) were isolated after simple cleavage of the chiral auxiliary.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Constrained C‐Glycosyl Amino Acid Derivatives Involving 1,3‐Dipolar Cycloaddition of Cyclic Nitrone as Key Step

et al. 2020

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“…It is worth to be mentioned that eq is commonly used to measure spin capturing constant C SC , so we suppose that all the previously measured constants were overestimated by the factor of 2.…”

Section: Resultsmentioning

confidence: 99%

Enhanced spin capturing polymerization: Numerical investigation of mechanism

Nikitin

Parkhomenko

Edeleva

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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Simulation on the kinetic scheme of enhanced spin capturing polymerizations (ESCP) were performed to reveal the influence of different parameters, e.g., initiation rate, spin capturing and side reactions on the properties (the monomer conversion, degree of polymerization, polydispersity index, and the fraction of “living” chains) of polymer obtained. The kinetic scheme of ESCP was solved numerically as well as the method of statistical moments of molecular weight distribution was applied to get some numerical expressions for analysis. The simulations showed that fast initiation rate can lead to decrease of living fraction and broadening of molecular weight distribution. Whereas high rate of spin capturing makes the polymer chains shorter but increases living character. And side reactions always decrease livingness of the polymer obtained. Finally in the case of absence of side reaction we were able to formulate criteria for formation of polymer with target molecular weight and quota of living chains via ESCP process. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2546–2556

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“…Preparation of Nitrones 1: Nitrones 1 were prepared by using a previously described sequence,18 starting from a glycine derivative and a ketone. The synthesis of 1b is reported below, the preparations of 1a 18b and 1c 16d have been described elsewhere.…”

Section: Methodsmentioning

confidence: 99%

Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization

et al. 2014

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International audienceNew chiral nitroxides based on the imidazolidin-4-one skeleton, and the corresponding hydroxylamines, have been prepared from cyclic nitrones by a straightforward reaction sequence. They were evaluated as catalysts in the aerobic oxidation of benzyl alcohol using different co-catalysts. Both the imidazolidinone nitroxides and hydroxylamines were proven to catalyze the reaction, with the ring substituent having an effect depending on the co-catalytic system. In some cases, rapid oxidation to benzaldehyde was accomplished at room temperature under an atmospheric O2 pressure. Moreover, atroposelective desymmetrization was achieved during the aerobic oxidation of a diol catalyzed by an enantiopure imidazolidinone nitroxide. Finally, the electrochemical behavior of the new hydroxylamines and nitroxides was investigated by cyclic voltammetry, which gave insights into the observed catalytic properties

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Enhanced Spin-capturing Polymerization and Radical Coupling Mediated by Cyclic Nitrones

Abstract: International audienc

Cited by 14 publications

References 22 publications

Synthesis of Constrained C‐Glycosyl Amino Acid Derivatives Involving 1,3‐Dipolar Cycloaddition of Cyclic Nitrone as Key Step

Synthesis of Constrained C‐Glycosyl Amino Acid Derivatives Involving 1,3‐Dipolar Cycloaddition of Cyclic Nitrone as Key Step

Enhanced spin capturing polymerization: Numerical investigation of mechanism

Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization

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