Characterization of methyl .alpha.-hydroxymethylacrylate ether cyclopolymer using nutation NMR spectroscopy

Mathias, Lon J.; Colletti, Ronald F.; Bielecki, Anthony

doi:10.1021/ja00005a014

Cited by 9 publications

(6 citation statements)

References 2 publications

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“…The strong absorption observed at 1680 cm −1 in Figure 2 indicates that the cyclic structure of the polymer is a five‐membered ring. The formation of a five‐membered ring in the polymer main chain was also reported for the cyclopolymerization of nonconjugated diene monomer such as the ether of methyl α‐hydroxymethylacrylate and ethyl α‐[(allyloxy)methyl]acrylate 9, 10.…”

Section: Resultsmentioning

confidence: 67%

Asymmetric cyclopolymerization ofN-tert-butyl-N-allylacrylamide in the presence of ?-cyclodextrin

Seno

Ikezumi

Sumie

et al. 2000

J. Polym. Sci. A Polym. Chem.

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The radical polymerization of N‐tert‐butyl‐N‐allylacrylamide (t‐BAA) was carried out in a dimethyl sulfoxide/H2O mixture in the presence of β‐cyclodextrin (β‐CD). The polymerization proceeded with the complete cyclization of the t‐BAA unit and yielded optically active poly(t‐BAA). The IR spectrum of the obtained polymer showed that the cyclic structure in the polymer was a five‐membered ring. The optical activity of poly(t‐BAA) increased with an increasing molar ratio of β‐CD to the t‐BAA monomer. The interaction of β‐CD with t‐BAA was confirmed by 1H NMR and 13C NMR analyses of the polymerization system. It is suggested that interaction of the t‐BAA monomer with the hydrophobic cavity of β‐CD plays an important role in the asymmetric cyclopolymerization of t‐BAA. The radical copolymerization of t‐BAA with styrene (St), methyl methacrylate, ethyl methacrylate, or benzyl methacrylate (BMA) also produced optically active copolymers with a cyclic structure from the t‐BAA unit. St and BMA carrying a phenyl group were predicted to compete with t‐BAA for interaction with β‐CD in the copolymerization system. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 2098–2105, 2000

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Section: Resultsmentioning

confidence: 67%

Asymmetric cyclopolymerization ofN-tert-butyl-N-allylacrylamide in the presence of ?-cyclodextrin

Seno

Ikezumi

Sumie

et al. 2000

J. Polym. Sci. A Polym. Chem.

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“…The mixture was stirred at ambient temperature for 1 h. The organic layer was separated and evaporated under reduced pressure to give 24.5 g of crude 5b (yield 93 %, purity 90 % by GC). Repeated vacuum distillation gave the pure diacrylate 5b as a clear viscous liquid in 48% yield: XH NMR (CDC13) 6 6.87 (s, 1H), 6.07 (s, 1H), 4.24 (q, 2H), 3.06 (s, 2H), 1.33 (t, 3H); 13C NMR (CDC13) 6 165.5, 133.0, 132.2,114.5, 61.7, 38.3, 37.7, 14.1.…”

Section: Methodsmentioning

confidence: 99%

New dicyano-containing cyclopolymers having high stereoregularity derived from dimethacrylmalononitrile

Tsuda¹,

Mathias²

1993

Macromolecules

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“…This leads to the conclusion that the monoene counterparts of SAMC have essentially no homopolymerization tendency, because it may be reasonably assumed that the other monofunctional counterparts of SAM C, ally! derivatives, have extremely low polymerizability based on 13 C NMR studies of the ally! group of SAMC shown later.…”

Section: Polymerization Of Samc and Spmcmentioning

confidence: 99%

“…Chemical shifts of C = C double bonds (CµH 2 =Ca<) and carbonyl carbons of the acryloyl groups of SAMC and related compounds obtained by measuring 13 C NMR spectra are summarized in Table III. be.…”

Section: Nmr Studies Of Samc and Related Compoundsmentioning

confidence: 99%

Cyclopolymerization XXIII. Design of Unconjugated Dienes with High Polymerizability Using Functional Groups with No Homopolymerization Tendency and Synthesis of Completely Cyclized Polymers Therefrom: Radical Polymerizations of N-Substituted N-Allyl-2-(methoxycarbonyl)allylamines

Liu

Kodaira

Urushisaki

et al. 1996

Polym J

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ABSTRACT:N-Substituted N-allyl-2-(methoxycarbonyl)allylamines (SAMC) were synthesized and polymerized to establish a methodology for designing unconjugated dienes with not only a high cyclization tendency but also high polymerizability. The N-substituents investigated were methyl, propyl, tert-butyl, and phenyl groups. Detailed examination of the properties of the unconjugated dienes reported so far indicated the use of functional groups with a higher conjugative nature together with no homopolymerization tendency to be essential to achieve this purpose. SAMC were designed since oc-substituted acrylates have a considerably higher conjugative nature, even if they do not have homopolymerization tendencies. In fact, conjugation between C=C and C=O double bonds of the acryloyl groups of SAMC and N-substituted N-propyl-2-(methoxycarbonyl)-allylamines (SPMC), one of the monofunctional counterparts of SAMC, were found to be considerably effective. No detectable homopolymer could be obtained from SPMC. It is well known that ally! compounds, the other monofunctional counterparts of SAMC, have extremely lower polymerization tendencies. SAMC were converted to completely cyclized polymers by use of a radical initiator with a high polymerization rate, especially in the case of methyl and propyl derivatives. Their polymerizabilities were correlated with the conjugative nature of C = C and C = 0 double bonds of their acryloyl groups, except for the phenyl derivative. ESR studies on the methyl derivative suggested that its polymerization initiates through the acryloyl group.

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Characterization of methyl .alpha.-hydroxymethylacrylate ether cyclopolymer using nutation NMR spectroscopy

Cited by 9 publications

References 2 publications

Asymmetric cyclopolymerization ofN-tert-butyl-N-allylacrylamide in the presence of ?-cyclodextrin

Asymmetric cyclopolymerization ofN-tert-butyl-N-allylacrylamide in the presence of ?-cyclodextrin

New dicyano-containing cyclopolymers having high stereoregularity derived from dimethacrylmalononitrile

Cyclopolymerization XXIII. Design of Unconjugated Dienes with High Polymerizability Using Functional Groups with No Homopolymerization Tendency and Synthesis of Completely Cyclized Polymers Therefrom: Radical Polymerizations of N-Substituted N-Allyl-2-(methoxycarbonyl)allylamines

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