A Magnetic Study of Polymerization Retardation

Ihrig, Judson L.; Alyea, Hubert N.

doi:10.1021/ja01108a038

Cited by 6 publications

(4 citation statements)

References 7 publications

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“…For compound 2, for example, the relative changes in 7 J HF and 6 J CF ties, acetone and DMSO are hydrogen bond acceptors, whilst MeOD is amphiprotic, e.g. As expected, C-6 of compounds 1α, 2α and 3α, and C-8 of 4α and 5α show a quite gation to purely rigid molecular structures, such as unsaturated and aromatic compounds, [17,18] or model compounds large 6 J CF value between the fluorine nucleus and C-6/8. For comparison, the same quantities for the one-bond J CF of 2α nor and acceptor.…”

Section: Resultssupporting

confidence: 63%

Experimental Evidence for Intramolecular Attractive Nonbonded C–F...H–C Interactions in 2′,3′-Dideoxy-4′-(fluoromethyl)nucleosides – Through-Space JCF and JHF NMR Coupling Constants, Correlation with Empirical Parameters of Solvent Polarity and Single-Crystal X-ray Structures

Vergani¹,

Viani²,

Meille³

et al. 1999

Eur. J. Org. Chem.

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Section: Resultssupporting

confidence: 63%

Experimental Evidence for Intramolecular Attractive Nonbonded C–F...H–C Interactions in 2′,3′-Dideoxy-4′-(fluoromethyl)nucleosides – Through-Space JCF and JHF NMR Coupling Constants, Correlation with Empirical Parameters of Solvent Polarity and Single-Crystal X-ray Structures

Vergani¹,

Viani²,

Meille³

et al. 1999

Eur. J. Org. Chem.

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“…Nevertheless, the technique has to be marked rather inefficient, since the polymerization proceeds slowly resulting in only 40% conversion after 48 hours of reaction time. The reason for this slow reaction lies in the nature of the monomer: As known from literature reports amines can function as retarders in free radical polymerizations 19, 20…”

Section: Resultsmentioning

confidence: 99%

“…The reason for this slow reaction lies in the nature of the monomer: As known from literature reports amines can function as retarders in free radical polymerizations. 19,20 When TMPMA is reacted with hydrochloric acid, the retarding amine-functionality is protonated and rendered innocuous. Polymerization of the ionic TMPMA-Cl 3 can be carried out in a mixture of water and ethanol (1:1) using the watersoluble 2,2 0 -azobis(2-methyl-propionamidine) dihydrochloride (VA067) as initiator at 50 C (Scheme 3, top).…”

Section: Free Radical Polymerizationmentioning

confidence: 99%

Polymerization of free secondary amine bearing monomers by RAFT polymerization and other controlled radical techniques

Janoschka

Teichler

Krieg

et al. 2012

J. Polym. Sci. A Polym. Chem.

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This work describes the polymerization of the free secondary amine bearing monomer 2,2,6,6‐tetramethylpiperidin‐4‐yl methacrylate (TMPMA) by means of different controlled radical polymerization techniques (ATRP, RAFT, NMP). In particular, reversible addition‐fragmentation chain transfer (RAFT) polymerization enabled a good control at high conversions and a polydispersity index below 1.3, thereby enabling the preparation of well‐defined polymers. Remarkably, the polymerization of the secondary amine bearing methacrylate monomer was not hindered by the presence of the free amine that commonly induces degradation of the RAFT reagent. Subsequent oxidation of the polymer yielded the polyradical poly(2,2,6,6‐tetramethylpiperidinyloxy‐4‐yl methacrylate), which represents a valuable material used in catalysis as well as for modern batteries. The obtained polymers having a molar mass (Mn) of 10,000–20,000 g/mol were used to fabricate well‐defined, radical‐bearing polymer films by inkjet‐ printing. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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“…It is not the purpose of this report to settle the problem of the point of attack of the free radical on the quinone molecule in polymerization reactions. This problem and the subsequent fate of the new radical formed are still in question (51,64,65). Price (75) proposed a nuclear attack, but there seems to be other evidence that attack occurs at the oxygen atoms (4, 18, 21, 27, 28, 66, 93).…”

Section: Mechanism Of Inhibiting Action Of Quinonesmentioning

confidence: 99%