Cationic Polymerization of Seven-Membered Cyclic Sulfites. Substituent Effect on the Polymerization Behavior

Azuma, Natsuhiro; Sanda, Fumio; Takata, Toshikazu; Endō, Takeshi

doi:10.1021/ma971082n

Cited by 5 publications

(2 citation statements)

References 14 publications

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“…Structurally varied 1-aryl-1,4-butanediols are of great synthetic value with immense applications in cationic polymerizations [34], as intermediates for the syntheses of important acyclic antiviral nucleosides [35] and cyclic ethers [36]. …”

Section: Resultsmentioning

confidence: 99%

“…From the results obtained so far, it is obvious that NaBH 4 in methanol can be efficiently used for the synthesis of 1-aryl-1,4-butanediols from the easily accessible 4-aryl-4-oxoesters ( Table 1 ) instead of employing the more costly and hazardous LiAlH 4 which also often gives rise to several non-identifiable by-products. Structurally varied 1-aryl-1,4-butanediols are of great synthetic value with immense applications in cationic polymerizations [ 34 ], as intermediates for the syntheses of important acyclic antiviral nucleosides [ 35 ] and cyclic ethers [ 36 ].…”

Section: Resultsmentioning

confidence: 99%

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Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride

Chaudhuri¹,

Saha²,

Saha³

et al. 2010

Beilstein J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride

Chaudhuri¹,

Saha²,

Saha³

et al. 2010

Beilstein J. Org. Chem.

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Synthesis and fundamental properties of methacrylate polymer containing five‐membered cyclic trithiocarbonate group

Nishi

Komeda

Aoyagi

et al. 2020

Journal of Polymer Science

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Abstract4‐(1,3‐Dithia‐2‐thioxocyclopenthyl)methacrylate (TCMA), containing the five‐membered trithiocarbonate moiety, was prepared from glycidyl methacrylate (GMA) through 2,3‐epithiopropyl methacrylate (ETMA). At first step, GMA was converted to ETMA by the reaction using thiourea. At second step, ETMA was reacted efficiently with carbon disulfide in the presence of a catalytic amount of 1,2‐dimethyltetrahydropyrimidine to give TCMA. The polymerization of TCMA proceeded under standard radical conditions to give the polymeric TCMA in 94% yield. The copolymerizations of TCMA with ethyl acrylate (EA) or acrylonitrile (AN) were conducted by changing the feed molar ratios of the monomers, in which the corresponding copolymers were obtained in over 83% yields. In addition, the obtained polymers showed the high values of refractive index over ca. 1.6 due to the presence of the cyclic trithiocarbonate structure.

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Substituent effect on the cationic ring‐opening polymerization of acyloxymethyl five‐member cyclic dithiocarbonates

Steblyanko

Choi

Sanda

et al. 2001

J. Polym. Sci. A Polym. Chem.

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Five-member cyclic dithiocarbonates were synthesized by the reactions of carbon disulfide with benzoic, p-anisic, p-chlorobenzoic, 1-naphthalenecarboxylic, pnitrobenzoic, and p-(tert-butyl)benzoic glycidyl esters, and their cationic ring-opening polymerizations were carried out with methyl trifluoromethane sulfonate and trifluoromethane sulfonic acid as initiators at room temperature to 80°C. Polymers with number-average molecular weights of 3400 -24,900 were obtained in high yields, and their structures were estimated by NMR and IR spectroscopy. The monomers showed a clear difference in the polymerization rate according to the substituents. The rate of polymerization decreased in the order of p-chlorobenzoic Ն benzoic Ͼ 1-naphthalenecarboxylic Ͼ p-nitro-benzoic Ͼ p-tert-butylbenzoic Ͼ p-anisic. The data of the reaction kinetics, NMR studies, and molecular orbital calculations proved a plausible mechanism involving the participation of p-substituted benzoyloxymethyl groups to stabilize the cationic propagating end. The polymers showed decomposition temperatures with 5% weight loss ranging from 200 to 260°C. No glass-transition temperatures for the polymers were observed below 200°C by differential scanning calorimetry.

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Cationic Polymerization of Seven-Membered Cyclic Sulfites. Substituent Effect on the Polymerization Behavior

Cited by 5 publications

References 14 publications

Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride

Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride

Synthesis and fundamental properties of methacrylate polymer containing five‐membered cyclic trithiocarbonate group

Substituent effect on the cationic ring‐opening polymerization of acyloxymethyl five‐member cyclic dithiocarbonates

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