The effect of SnCl
 4
 on the radical polymerization of
 N
 ‐allyl‐
 N
 ‐phenylmethacrylamide and
 N
 ‐allyl‐
 N
 ‐phenylacrylamide

Seno, Makiko; Kawamura, Yuta; Sato, Tsuneyuki

doi:10.1002/(sici)1099-0518(19961115)34:15<3121::aid-pola3>3.0.co;2-#

Cited by 5 publications

(27 citation statements)

References 24 publications

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“…As reported in the earlier paper, 15 the presence of SnCl 4 was observed to cause an appreciable change in the reactivity of PAMA in its homo-and copolymerization, where the 1:1 and 1:2 complexes between SnCl 4 and PAMA were confirmed to be formed by 1 H-NMR spectroscopy. 15 Table 2 presents the results observed in the photopolymerization of PAMA with MAIB at room temperature in benzene in the presence of SnCl 4 and L-menthol. The L-menthol concentration was changed from 1 to 5 times the monomer concentration, keeping [PAMA] ) [SnCl 4 ] ) 0.50 mol L -1 constant.…”

Section: Resultssupporting

confidence: 78%

“…The same cyclic structure was also contained in the polymers formed in the homopolymerizations of PAMA without any additives and in the presence of SnCl 4 alone. 15 The specific rotation of the resulting polymers was measured in THF at room temperature. As shown in Table 1, the polymers showed no optical activity.…”

Section: Resultsmentioning

confidence: 99%

“…Next, the polymerization of PAMA with MAIB was performed in the presence of SnCl 4 and L-menthol. As reported in the earlier paper, 15 the presence of SnCl 4 was observed to cause an appreciable change in the reactivity of PAMA in its homo-and copolymerization, where the 1:1 and 1:2 complexes between SnCl 4 and PAMA were confirmed to be formed by 1 H-NMR spectroscopy. 15 Table 2 presents the results observed in the photopolymerization of PAMA with MAIB at room temperature in benzene in the presence of SnCl 4 and L-menthol.…”

Section: Resultsmentioning

confidence: 99%

“…16,17 In an earlier paper we studied the effect of SnCl 4 on the radical cyclopolymerization of PAMA. 15 Recently we have tried to cause asymmetric induction by cyclohomoand cyclocopolymerizations of PAMA in the presence of SnCl 4 and L-menthol as a chiral compound. The present paper describes the results observed in the asymmetric polymerizations of PAMA where dimethyl 2,2′-azobis-(isobutyrate) (MAIB) was used as initiator.…”

Section: Introductionmentioning

confidence: 85%

“…[13][14][15] Such cyclopolymerizations are also expected to produce asymmetric centers in the resulting polymers. Cyclopolymerization of 1,5-pentadiene with an optically active metallocene catalyst was found to yield optically active polymer.…”

Section: Introductionmentioning

confidence: 93%

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Asymmetric Radical Cyclopolymerization of N-Allyl-N-phenylmethacrylamide in the Presence of SnCl₄ and l-Menthol

1997

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Asymmetric induction was examined in the cyclopolymerization and cyclocopolymerization of N-allyl-N-phenylmethacrylamide (PAMA) with dimethyl 2,2′-azobis(isobutyrate) in benzene in the presence of L-menthol and SnCl4. Optical activity ([R]D ) -0.3 to -5.6) was observed for poly(PAMA)s formed in the radical polymerization of the PAMA/SnCl4/L-menthol system. The PAMA monomer unit was incorporated exclusively as a five-membered ring into the highly cyclized poly(PAMA)s (degree of cyclization (DC) ) 95-98%) obtained. The radical copolymerization of PAMA with methyl methacrylate in the presence of L-menthol and SnCl4 also gave optically active copolymers, the PAMA units of which were similarly highly cyclized (DC ) 90-94%) as a five-membered ring. The [R]D value of the copolymer increased up to [R]D ) -15.2 with increasing PAMA concentration in the feed. The much lower DC values (25-68%) of the PAMA monomer unit were observed for the copolymers formed in the copolymerization of the PAMA/styrene/L-menthol/SnCl4 system. However, the copolymers showed a considerable optical activity ([R]D ) -9.1 to -11.8).

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Section: Resultssupporting

confidence: 78%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 85%

Section: Introductionmentioning

confidence: 93%

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Asymmetric Radical Cyclopolymerization of N-Allyl-N-phenylmethacrylamide in the Presence of SnCl₄ and l-Menthol

1997

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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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Synthesis and characterization of poly(N‐phenyl methacrylamide‐co‐methyl methacrylate) and reactivity ratios determination

Reddy

Naidu

Reddy³

2003

J of Applied Polymer Sci

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Free-radical solution copolymerization of Nphenyl methacrylamide and methyl methacrylate in various feed ratios was done using a benzoyl peroxide initiator in N,N-dimethylformamide at 70°C. The structure of the copolymer was elucidated by infrared and proton nuclear magnetic resonance spectroscopy. The copolymer composition was determined from the corresponding 1 H-NMR spectra of the copolymers. Finemann-Ross and Kelen-Tudos methods were used to determine the reactivity ratios of the monomers. The molecular weight distribution of the copolymers was determined using gel permeation chromatography. Thermal properties of the copolymers were determined using differential scanning calorimetry and thermogravimetric analysis (TGA). The activation energy for thermal degradation of the copolymers was determined from the TGA data.

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The effect of SnCl ₄ on the radical polymerization of N ‐allyl‐ N ‐phenylmethacrylamide and N ‐allyl‐ N ‐phenylacrylamide

Cited by 5 publications

References 24 publications

Asymmetric Radical Cyclopolymerization of N-Allyl-N-phenylmethacrylamide in the Presence of SnCl₄ and l-Menthol

Asymmetric Radical Cyclopolymerization of N-Allyl-N-phenylmethacrylamide in the Presence of SnCl₄ and l-Menthol

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

Synthesis and characterization of poly(N‐phenyl methacrylamide‐co‐methyl methacrylate) and reactivity ratios determination

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The effect of SnCl 4 on the radical polymerization of N ‐allyl‐ N ‐phenylmethacrylamide and N ‐allyl‐ N ‐phenylacrylamide

Cited by 5 publications

References 24 publications

Asymmetric Radical Cyclopolymerization of N-Allyl-N-phenylmethacrylamide in the Presence of SnCl4 and l-Menthol

Asymmetric Radical Cyclopolymerization of N-Allyl-N-phenylmethacrylamide in the Presence of SnCl4 and l-Menthol

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

Synthesis and characterization of poly(N‐phenyl methacrylamide‐co‐methyl methacrylate) and reactivity ratios determination

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Resources

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The effect of SnCl ₄ on the radical polymerization of N ‐allyl‐ N ‐phenylmethacrylamide and N ‐allyl‐ N ‐phenylacrylamide

Asymmetric Radical Cyclopolymerization of N-Allyl-N-phenylmethacrylamide in the Presence of SnCl₄ and l-Menthol

Asymmetric Radical Cyclopolymerization of N-Allyl-N-phenylmethacrylamide in the Presence of SnCl₄ and l-Menthol