Cationic isomerization and ring-opening polymerization of a five-membered dithiocarbonate: The first example for control of isomerization and polymerization

Choi, Wonmun; Sanda, Fumio; Kihara, Nobuhiro; Endō, Takeshi

doi:10.1002/(sici)1099-0518(199712)35:17<3853::aid-pola24>3.0.co;2-b

Cited by 30 publications

(21 citation statements)

References 2 publications

(1 reference statement)

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“…The monomer 1 selectively isomerizes to 4 in the presence of Lewis acids such as ZnCl 2 and SnCl 4 , and protonic acids such as CF 3 SO 3 H (TfOH) and CH 3 SO 3 H as the catalysts, whereas 1 selectively polymerizes with CF 3 SO 3 -Me (TfOMe) and CF 3 SO 3 Et (TfOEt) as the initiators to afford the corresponding polydithiocarbonates (5) (Scheme 1). 11 The formation of a cyclic oxonium cation (2) and a cyclic carbenium cation (3) has been confirmed in the reactions of 1 with TfOH and TfOMe, respectively (Scheme 1). 12 The selectivity of the cationic isomerization and polymerization of 1 is attributable to the different intermediates depending on the catalysts.…”

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confidence: 83%

A Novel Construction of Living Polymerization by Neighboring Group Participation: Living Cationic Ring-Opening Polymerization of a Five-Membered Cyclic Dithiocarbonate

1998

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confidence: 83%

A Novel Construction of Living Polymerization by Neighboring Group Participation: Living Cationic Ring-Opening Polymerization of a Five-Membered Cyclic Dithiocarbonate

1998

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“…Polydithiocarbonate can also be obtained from the interfacial polycondensation of dichloroformate and dithiol or from phosgene and dithiol . Alternatively, cyclic dithiocarbonates also undergo cationic ring‐opening polymerization to afford polydithiocarbonates …”

Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

254

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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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“…DTC undergoes the cationic ROP by using alkyl triflate as an initiator (Scheme 22). 65,66 The formed polymer has ASA(C¼ ¼O)SA linkage, which is the isomeric form of AS(C¼ ¼S)OA in the monomer, as a result of the isomerization process involved in the polymerization mechanism. Interestingly, the corresponding polymer can be cationically and anionically depolymerized, leading to the selective formation of an isomer of DTC (¼ DTC 0 ).…”

Section: Decrosslinking Based On Depolymerization Accompanied By Isommentioning

confidence: 99%

Development and application of novel ring‐opening polymerizations to functional networked polymers

Endō

Sudo

2009

J. Polym. Sci. A Polym. Chem.

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This Highlightgives an overview of the recent progress in development of new ring-opening polymerizations (ROPs) and their applications to functional networked polymers in our group. The described ROPs involve thermally induced polymerization of 1,3-benzoxazine, anionic alternating copolymerizations of epoxides and lactones, and those exhibiting equilibrium nature. These ROPs were successfully applied to the syntheses of the relevant networked polymers, leading to their distinctive features such as high thermal stability, small volume shrinkage, and selective decrosslinking ability, which enabled design and development of next generation materials.

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Cationic isomerization and ring-opening polymerization of a five-membered dithiocarbonate: The first example for control of isomerization and polymerization

Cited by 30 publications

References 2 publications

A Novel Construction of Living Polymerization by Neighboring Group Participation: Living Cationic Ring-Opening Polymerization of a Five-Membered Cyclic Dithiocarbonate

A Novel Construction of Living Polymerization by Neighboring Group Participation: Living Cationic Ring-Opening Polymerization of a Five-Membered Cyclic Dithiocarbonate

Sulfur Chemistry in Polymer and Materials Science

Development and application of novel ring‐opening polymerizations to functional networked polymers

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