Polythioamides aliphatiques—I

Gressier, J.C.; Lévesque, Guy

doi:10.1016/0014-3057(80)90230-x

Cited by 17 publications

(11 citation statements)

References 28 publications

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“…In‐depth literature survey indicates that the initial studies on the synthesis of polythioamides are based on the condensation reaction of dithioesters (or didithioesters) with diamines ( Scheme ) . By taking advantage of this approach diverse aliphatic, semi‐aromatic and fully‐aromatic polythioamide derivatives were synthesized.…”

Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

258

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%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

258

220

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“…We have previously synthesized several bis(dithioester)s to prepare poly(thioamide)s through a room-temperature condensation reaction with diamines. [51][52][53] For such a purpose, these bis(dithioester)s need to be obtained in a high purity grade, preferentially in a crystalline form, so we have often preferred long chain alkyl or carboxymethyl bis(dithioester)s.…”

Section: Protein Modifications Through Reactions On Lysinementioning

confidence: 99%

“…The first bis(dithioester)s 52 were prepared from dinitriles using a modification of the method of Marvel et al 54 The first step consists of the addition of a thiol on the nitrile triple bond, the presence of anhydrous hydrogen chloride being required to complete the formation of the imidoester as an imidium salt (Figure 5). Improvements lie in the use of anhydrous conditions and eventually of insoluble polymeric pyridine (cross-linked polyvinylpyridine) instead of pyridine for the second step (sulfhydrolysis of the imidium salt).…”

Section: Protein Modifications Through Reactions On Lysinementioning

confidence: 99%

“…1 H NMR (CDCl 3 ): 1.30 (9H, t J ) 7 Hz, CH 3 ), 1.60 (2H, dt J HH ) 7 Hz, CH 3 ), 1.60 (2H, dt J HH ) 7 Hz, J HP ) 20 Hz, PCH 2 ), 1.00-2.00 (4H, m, CH 2 ), 3.00 (2H, t, J ) 7 Hz 2H, CH 2 CS 2 ), 3.15 (2H, q J ) 6 Hz, SCH 2 ), 4.10 (4H, dq J HOP ) J HH ) 7 Hz, OCH 2 ). 13 (15), 253 (24), 237 (54), 193 (12), 179 (56), 165 (25), 152 (81), 137 (48), 81 (52), 71 (35), 55 (100), 41 (30).…”

Section: Diethyl [4-(ethylthiothiocarbonyl)]butylphosphonate (13b)mentioning

confidence: 99%

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Protein Thioacylation. 1. Reagents Design and Synthesis

et al. 2000

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Thioacylation is a new way for protein chemical modification. Carboxylic dithioesters and -acids react selectively and rapidly at room temperature with aliphatic amines such as lysine epsilon-amino groups leading to thioamide formation, without any other reagent or catalyst. Various thioacylating reagents were synthesized: monofunctional dithioesters bearing on the acylating end various chemical groups such as: aliphatic chains, phenyl group, mono- and dicarboxylic acids, dialkylphosphonic ester, phosphonic acid, thiol, phenol, or quaternary ammonium group. Bifunctional dithioesters containing either a polymethylene chain or an ethylene oxide oligomer as spacer group as well as some mono- and bis(dithio acids) are described. Applications of thioacylation may be involved either in enzyme chemical modifications or in the obtention of new materials from proteins. Bifunctional reagents might be used as cross-linking or coupling reagents.

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“…in our group was mainly devoted to the synthesis Leuckart 12,13 was the first to use aluminium of main-chain polythioamides from diamines and chloride as the catalyst in the reaction of isocyabis(dithioesters). [1][2][3][4][5][6][7][8][9][10] Levesque et al have prepared nates with aromatic hydrocarbons. However, the many aliphatic polythioamides from bis(dithiocorresponding anilide was obtained in low yield.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of thioamide-containing polystyrenes by Friedel-Crafts reaction and by thioamidation of (co)polydithioesters

Tabak

Pham

Lévesque

et al. 1998

J. Polym. Sci. A Polym. Chem.

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Thioamide groups were introduced into polystyrenes by the Friedel–Crafts reaction, with phenyl isothiocyanate in nitromethane solution, in the presence of anhydrous aluminium chloride. Free radical copolymerization of 4‐vinyl dithiobenzoate with styrene followed by low‐temperature solution condensation reactions, with excess of amines in N,N‐dimethylformamide, offered another synthetic route to (co)polymers containing thioamine groups in the side chains without crosslinking. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 117–127, 1998

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Polythioamides aliphatiques—I

Cited by 17 publications

References 28 publications

Sulfur Chemistry in Polymer and Materials Science

Sulfur Chemistry in Polymer and Materials Science

Protein Thioacylation. 1. Reagents Design and Synthesis

Synthesis of thioamide-containing polystyrenes by Friedel-Crafts reaction and by thioamidation of (co)polydithioesters

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