Copolymerization of propylene oxide and carbon disulfide with diethylzinc–electron‐donor catalyst

Adachi, Nobuo; Kida, Yasuji; Shikata, Kazuo

doi:10.1002/pol.1977.170150415

Cited by 43 publications

(25 citation statements)

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“…Traditional preparation of polythiocarbonates generally involves: A) the reaction of thiophosgene and diphenol derivatives; B) the condensation of dithiol with dichloroformate derivatives; C) the ROP of five, six, and seven‐membered cyclic monothiocarbonates; or D) alternating copolymerization of cyclic ether derivatives (e.g., oxirane, oxetane) with CS 2 or COS ( Scheme A–D, respectively).…”

Section: Chemistrymentioning

confidence: 99%

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Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

278

220

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The ORCID identification number(s) for the author(s) of this article can be found under https://doi.org/10.1002/marc.201800650. ChemistryBefore moving to the recent advances within the last 5 years in the diverse applications of sulfur chemistry in polymer and Sulfur-Containing PolymersSulfur and its functional groups are major players in an area of exciting research taking place in modern polymer and materials science, both in academia and industry. In fact, manifold sulfur-based reactions that are both exceptionally versatile as well as tremendously useful have been implemented, and further utilized for the design and preparation of polymeric materials that lead to a plethora of applications ranging from medicine to optics and nanotechnology to separation science. Hence, within this review, an overview of strategies and developments used over the last 5 years to reinforce the importance of the sulfur functional group in modern polymer and materials science is presented. In particular, many important references in the primary literature of sulfur chemistry are referred to, including thiol-ene, thiol-yne, thiol-Michael addition, disulfide cross-linking, and thiol-disulfide exchange, among others, by explaining and illustrating the important principles. Last but not least, the grand aim to underpin the importance of sulfur in modern polymer and materials science is achieved by presenting selected examples in diverse fields and postulating the respective potential for real-world applications. he is now a full professor at KIT.sulfur atoms, and tetraphenylethene-bearing di(alkyl bromide) (Scheme 3). The yield of the polymerization was dependent on the di(alkyl bromide) monomer; the longer spacer between the aromatic moiety and the reactive bromide end groups Scheme 1. The discussion henceforth focuses on the synthesis of polymers possessing the depicted sulfur functional groups. Scheme 2.Representative examples of polythioethers prepared via A) the nucleophilic substitution reaction between an electrophilic dihalide with nucleophilic derivatives of dithiols under alkaline conditions; B) the thiol-ene/yne addition reaction between AA and BB type monomers (i.e., dithiols and dienes/diynes); and C) radical or ionic ring-opening of sulfurcontaining strained rings.Scheme 3. The thiol-bromo polymerization of conformationally fixed monomers to provide multifunctional polymers. [19] Macromol. Rapid Commun. 2019, 40, 1800650 Scheme 4. The regioselective selective nucleophilic aromatic substitution between thiol and fluorinated aromatic compounds, the para-fluorothiol reaction (PFTR).Scheme 5. Synthesis of a linear polymer via PFTR-reaction. [21]

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Section: Chemistrymentioning

confidence: 99%

“…The base‐catalyzed direct coupling of CS 2 with epoxides to synthesize poly(thiocarbonate)s was initially reported by Adachi et al. in 1977 . (Scheme D).…”

Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

278

220

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“…Similarly, carbon disulfide and propylene oxide reactions are catalyzed by magnesium oxide to yield episulfides (73), and by derivatives of diethylzinc to yield low-molecular-weight copolymers (74). Use of tertiary amines as catalysts under pressure produces propylene trithiocarbonate (75).…”

Section: Carbon Dioxide and Carbon Disulfidementioning

confidence: 99%

Propylene Oxide

Trent¹

2001

Kirk-Othmer Encyclopedia of Chemical Technology

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Propylene oxide [75-56-9] (methyloxirane, 1,2-epoxypropane) is a significant organic chemical used primarily as a reaction intermediate for production of polyether polyols, propylene glycol, alkanolamines (qv), glycol ethers, and many other useful products (see Glycols). Propylene oxide was first prepared in 1861 by Oser and first polymerized by Levene and Walti in 1927 (1). Propylene oxide is manufactured by two basic processes: the traditional chlorohydrin process (see Chlorohydrins) and the hydroperoxide process, where either tert-butanol (see Butyl alcohols) or styrene (qv) as a co-product.

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“…An efficient method for synthesizing cyclic thiocarbonates is performed by the coupling reaction of carbon disulfide (CS 2 ) with epoxides. Depending on the catalysts and reaction conditions, five‐membered cyclic dithiocarbonate 2 , its regioisomers 3 and 4 , trithiocarbonate 5 and episulfide 6 have been reported to be formed (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

“…Depending on the catalysts and reaction conditions, five-membered cyclic dithiocarbonate 2, its regioisomers 3 and 4, trithiocarbonate 5 and episulfide 6 have been reported to be formed (Scheme 1 ). [4][5][6][7][8][9] In recent decades, many catalyst systems, including amines, alkali metal salts and quaternary ammonium salts, potassium alcoholates and transition metal complexes, have been developed for this transformation. [4,5,[10][11][12][13] Although the advances have been significant, these systems suffered from low catalyst activities, the use of solvent or the requirement for high catalyst loading.…”

Section: Introductionmentioning

confidence: 99%

Cooperative catalysis with binary Lewis acid–Lewis base system for the coupling of carbon disulfide and epoxides

Wang

et al. 2012

Applied Organom Chemis

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The cycloaddition of epoxides with carbon disulfide proceeds effectively by using a binary catalyst system of tetradentate Schiff‐base aluminum complexes (designated as salenAlX) as Lewis acid in connection with a nucleophilic co‐catalyst, such as quaternary ammonium salt. The steric factor of the substituent groups on the aromatic rings of salenAlX and the anion of quaternary ammonium salt all have significant effects on the activity of the binary catalyst system, as well as the selectivities of the resultant cyclic products. The effects of temperature, time and the molar ratio of reactants were also investigated in detail with regard to propylene oxide with carbon disulfide, and a plausible mechanism was proposed. Copyright © 2012 John Wiley & Sons, Ltd.

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Copolymerization of propylene oxide and carbon disulfide with diethylzinc–electron‐donor catalyst

Cited by 43 publications

References 1 publication

Sulfur Chemistry in Polymer and Materials Science

Sulfur Chemistry in Polymer and Materials Science

Propylene Oxide

Cooperative catalysis with binary Lewis acid–Lewis base system for the coupling of carbon disulfide and epoxides

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