2-Phenyl-1,3-butadiene and Related Compounds<sup>1</sup>

Marvel, C. S.; Woolford, R. G.

doi:10.1021/jo01105a019

Cited by 28 publications

(10 citation statements)

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“…trans-1-Phenyl-1,3-butadiene (1-PB) was prepared as in a previous paper. 1 2-Ph en y 1-1,3butadiene was synthesized from the corresponding alcohol prepared according to the method of Marvel, et a/., 5 and the subsequent dehydration by potassium bisulfate: bp 62-65°C (23 mm) [lit. 5 bp 57-63°C (13 mm)].…”

Section: Methodsmentioning

confidence: 99%

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Cationic Polymerization of Phenylbutadienes. II. Initiation Reaction in Cationic Polymerization of Phenylbutadienes Catalyzed by Triphenylmethylstannic Pentachloride

Asami

Hasegawa

1976

Polym J

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Initiation in cationic polymerization of phenyl-substituted 1,3-butadienes with triphenylmethylstannic pentachloride as catalyst was studied. The rates of consumption of Ph3CSnCls with !-phenyl-substituted butadienes are represented by the following equation-d[Ph3CSnCls]ldt=k/[PhaCSnClo][M] , where M means monomer. On the other hand, in the case of 2-phenyl-substituted butadienes the rate is represented as follows-d[PhsCSnClsldt=k/[PhaCSnCls][M] + k[PhsCSnCls]([M]o-[M]) and the formation of a rr-complex between the monomer and a carbonium ion is suggested. The initiation rate constants decreased according to the following order: 1-phenyl-1,3-butadiene > 2-phenyl-1,3-butadiene > 1, 1-diphenyl-1 ,3-butadiene > 1 ,2-diphenyl-1 ,3-butadiene > 2,3-diphenyl-1 ,3-butadiene. 1,4-Diphenyl-1,3-butadiene did not react with PhsCSnCls at all. The high reactivity of phenylbutadienes toward PhsCSnCls in comparison with that of vinyl monomers could be ascribed to the stabilization of allyl-type cations which were formed by an attack of a trityl cation onto the 4-position and the !-position carbon for 1-phenylbutadienes and 2-phenylbutadiene, respectively.

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Section: Methodsmentioning

confidence: 99%

“…1 2-Ph en y 1-1,3butadiene was synthesized from the corresponding alcohol prepared according to the method of Marvel, et a/., 5 and the subsequent dehydration by potassium bisulfate: bp 62-65°C (23 mm) [lit. 5 bp 57-63°C (13 mm)]. 1,1-Diphenyl-1,3-butadiene (1,1-DPB) was prepared according to the method of Eisch and Husk: 6 mp 38.5-39.0°C…”

Section: Methodsmentioning

confidence: 99%

Cationic Polymerization of Phenylbutadienes. II. Initiation Reaction in Cationic Polymerization of Phenylbutadienes Catalyzed by Triphenylmethylstannic Pentachloride

Asami

Hasegawa

1976

Polym J

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“…13 Mixture of (AE)-3,6-Dihydro-5-phenyl-1,2-oxathiin 2-Oxide (5g) and (AE )-3,6-Dihydro-4-phenyl-1,2-oxathiin 2-Oxide (6g). As described for 5f/6f, with 2-phenylbuta-1,3-diene (4g) [8]. At À 808, the equilibrium 4g SO 2 > 5g was reached in ca.…”

Section: Experimental Partmentioning

confidence: 90%

Competition between Hetero-Diels-Alder and Cheletropic Additions of Sulfur Dioxide to 2-Substituted Buta-1,3-dienes. Synthesis of 2-(1-Naphthyl)- and 2-(2-Naphthyl)buta-1,3-diene

Roversi¹,

Vogel²

2002

HCA

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Chloroprene ( 2-chlorobuta-1,3-diene; 4b) and electron-rich dienes such as 2-methoxy-(4c), 2-acetoxy-(4d), and 2-(phenylseleno)buta-1,3-diene (4e) refused to equilibrate with the corresponding sultines 5 or 6 between À 80 and À 108 in the presence of excess SO 2 and an acidic promoter. Isoprene (4a) and 2-(triethylsilyl)-(4f), 2-phenyl-(4g), and 2-(2-naphthyl)buta-1,3-diene (4i) underwent the hetero-Diels-Alder additions with SO 2 at low temperature. In contrast, 2-(1-naphthyl)buta-1,2-diene (4h) did not. With dienes 4a, 4g, and 4i, the heteroDiels-Alder additions with SO 2 gave the corresponding 4-substituted sultine 5 with high regioselectivity. In the case of 4g SO 2 >5g, the energy barrier for isomerization of 5g to 5-phenylsultine (6g) was similar to that of the cheletropic addition of 4g to give 3-phenylsulfolene (7g). The hetero-Diels-Alder addition of 4f gave a 1 : 4 mixture of the 4-(triethylsilyl)sultine (5f) and 5-(triethylsilyl)sultine (6f). The preparation of the two new dienes 4h and 4i is reported. Introduction. ± In the two preceding reports [1] [2], we have demonstrated that the competition between hetero-Diels-Alder and cheletropic additions of sulfur dioxide depends strongly on the nature of the conjugated dienes. At low temperature (À 808) and in the presence of an acidic promoter, SO 2 adds to (E)-1-alkylbuta-1,3-diene (E)-1a giving, in agreement with the endo Alder rule [2], the corresponding cis-6-alkyl-2,6-dihydro-1,2-oxathiin 2-oxides (cis-sultines c-2a), which then equilibrate with their more stable trans-isomers (trans-sultines t-2a) (Scheme 1).

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“…Moreover, Poly(2-PB) can also be used to produce high-temperature thermoplastics with a Tg as high as 325 °C [114]. Since the successful synthesis of 2-PB by Marvel, [115] it received much attention [116,117]. Firstly, methylmagnesium iodide is prepared by adding methyl iodide and magnesium into diethyl ether.…”

Section: Synthesis Of 2-phenyl-13-butadienesmentioning

confidence: 99%

Synthesis of 1,3-Butadiene and Its 2-Substituted Monomers for Synthetic Rubbers

Liu

et al. 2019

Catalysts

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Synthetic rubbers fabricated from 1,3-butadiene (BD) and its substituted monomers have been extensively used in tires, toughened plastics, and many other products owing to the easy polymerization/copolymerization of these monomers and the high stability of the resulting material in manufacturing operations and large-scale productions. The need for synthetic rubbers with increased environmental friendliness or endurance in harsh environments has motivated remarkable progress in the synthesis of BD and its substituted monomers in recent years. We review these developments with an emphasis on the reactive routes, the products, and the synthetic strategies with a scaling potential. We present reagents that are primarily from bio-derivatives, including ethanol, C4 alcohols, unsaturated alcohols, and tetrahydrofuran; the major products of BD and isoprene; and the by-products, activities, and selectivity of the reaction. Different catalyst systems are also compared. Further, substituted monomers with rigid, polar, or sterically repulsive groups, the purpose of which is to enhance thermal, mechanical, and interface properties, are also exhaustively reviewed. The synthetic strategies using BD and its substituted monomers have great potential to satisfy the increasing demand for better-performing synthetic rubbers at the laboratory scale; the laboratory-scale results are promising, but a big gap still exists between current progress and large scalability.

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2-Phenyl-1,3-butadiene and Related Compounds¹

Cited by 28 publications

References 0 publications

Cationic Polymerization of Phenylbutadienes. II. Initiation Reaction in Cationic Polymerization of Phenylbutadienes Catalyzed by Triphenylmethylstannic Pentachloride

Cationic Polymerization of Phenylbutadienes. II. Initiation Reaction in Cationic Polymerization of Phenylbutadienes Catalyzed by Triphenylmethylstannic Pentachloride

Competition between Hetero-Diels-Alder and Cheletropic Additions of Sulfur Dioxide to 2-Substituted Buta-1,3-dienes. Synthesis of 2-(1-Naphthyl)- and 2-(2-Naphthyl)buta-1,3-diene

Synthesis of 1,3-Butadiene and Its 2-Substituted Monomers for Synthetic Rubbers

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2-Phenyl-1,3-butadiene and Related Compounds1

Cited by 28 publications

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Cationic Polymerization of Phenylbutadienes. II. Initiation Reaction in Cationic Polymerization of Phenylbutadienes Catalyzed by Triphenylmethylstannic Pentachloride

Cationic Polymerization of Phenylbutadienes. II. Initiation Reaction in Cationic Polymerization of Phenylbutadienes Catalyzed by Triphenylmethylstannic Pentachloride

Competition between Hetero-Diels-Alder and Cheletropic Additions of Sulfur Dioxide to 2-Substituted Buta-1,3-dienes. Synthesis of 2-(1-Naphthyl)- and 2-(2-Naphthyl)buta-1,3-diene

Synthesis of 1,3-Butadiene and Its 2-Substituted Monomers for Synthetic Rubbers

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2-Phenyl-1,3-butadiene and Related Compounds¹