Novel polyaddition system for poly(dithiohydantoin) through zwitter ion derived from diisothiocyanate and tetraaminoethylene

Sudo, Atsushi; Igarashi, Kenji; Endō, Takeshi

doi:10.1002/1099-0518(20001201)38:23<4200::aid-pola50>3.0.co;2-x

Cited by 3 publications

(3 citation statements)

References 10 publications

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“…12,13 Spiro derivatives of such heterocycles have attracted special attention as potential aldose reductase inhibitors 14 or antileishmaniasis agents. 10 Although reports of such molecules are increasing, [15][16][17][18] less than 20 reported dithiohydantoin derivatives [19][20][21][22][23][24][25][26][27] of the type shown in Fig. 1 have been located.…”

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Thermal fragmentation of spirodithiohydantoins: A novel route to NHCs

et al. 2013

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Spirodithiohydantoins undergo a two-step thermal fragmentation affording zwitterionic betaine intermediates and N-heterocyclic carbenes (NHCs) respectively. Such reactions are novel, occur under mild conditions and give NHCs in high yield and purity. This phenomenon was studied using various spectroscopic techniques and control experiments with elemental sulfur.Quantum chemical calculations were employed to provide a deeper understanding of such transformations.

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Thermal fragmentation of spirodithiohydantoins: A novel route to NHCs

et al. 2013

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“…On the other hand, the diisothiocyanates, which are less reactive toward several nucleophilic agents and more stable in ambient moisture and air atmosphere than that of the diisocyanate, can be used for the polyaddition of various diols, diamines, and dithiols as well as the diisocyanates . The polyaddition of diisothiocyanates with diols and/or diamines affords polythiourethanes and/or polythioureas, which are especially utilized as the optical materials due to high refractive index and transparency .…”

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confidence: 99%

“…[11][12][13] On the other hand, the diisothiocyanates, which are less reactive toward several nucleophilic agents and more stable in ambient moisture and air atmosphere than that of the diisocyanate, [14][15][16] can be used for the polyaddition of various diols, diamines, and dithiols as well as the diisocyanates. [17][18][19][20][21] The polyaddition of diisothiocyanates with diols and/or diamines affords polythiourethanes and/or polythioureas, which are especially utilized as the optical materials due to high refractive index and transparency. [22][23][24][25][26][27] Moreover, we have demonstrated that polythiourethanes having the mercaptothiourethane moiety are selectively obtained from bifunctional cyclic dithiocarbonates and diamines without formation of hydroxydithiourethane.…”

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confidence: 99%

Synthesis of polydithiourethanes and their thermal, optical, and mechanical properties originated from monomers structure

Yoshida¹,

Endō²

2018

J. Polym. Sci. Part A: Polym. Chem.

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Polyaddition of various diisothiocyanates and dithiols was achieved with triethylamine in dimethylformamide at 25 °C for 12 h under nitrogen, and then the corresponding polydithiourethanes (PDTUs) were obtained with high yield and molecular weight without depending on the monomer structures, although the dithiol monomer of the low nucleophilicity was unsuitable for polyaddition in this system. The chemical and physical properties of the obtained PDTUs such as solvent solubility, glass transition temperature, thermal stability, transparency, refractive index, and tensile strength, were analyzed in detail by gel permeation chromatography, nuclear magnetic resonance, Fourier transform infrared–attenuated total reflection, ultraviolet–visible, differential scanning calorimetry, thermogravimetric analysis, and tensile testing measurements. These results proved that PDTUs and their cast films having the aliphatic diisothiocyanate and dithiol moieties exhibited excellent chemical and physical properties compared to that of the aromatic PDTUs. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 2255–2262

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An unprecedented tandem 1,3-dipolar cycloaddition–cheletropic elimination: a facial approach to novel push–pull olefins

Zhu¹,

Liu²,

Wang³

et al. 2007

Org. Biomol. Chem.

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The interaction of 2-(phenylthiocarbamoyl) imidazolium inner salts with dimethyl acetylenedicarboxylate produced dimethyl 2-(imidazolin-2-ylidene)-3-thioxobutanedioates in moderate to good yields. The process involved a tandem reaction comprising a 1,3-dipolar cycloaddition and an unprecedented cheletropic elimination of the phenyl isonitrile from a 2-phenyliminodihydrothiophene moiety. NMR and X-ray diffraction studies confirmed that the 2-(imidazolin-2-ylidene)-3-thioxobutanedioates are novel push-pull olefins and have potential applications in nonlinear optical materials.

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Novel polyaddition system for poly(dithiohydantoin) through zwitter ion derived from diisothiocyanate and tetraaminoethylene

Abstract: A novel polyaddition system was developed based on the reaction of diisothiocyanate with tetraaminoethylene. The reaction proceeded through a corresponding zwitterionic intermediate that reacted with isothiocyanate to afford polymers with dithiohydantoin moiety.

Cited by 3 publications

References 10 publications

Thermal fragmentation of spirodithiohydantoins: A novel route to NHCs

Thermal fragmentation of spirodithiohydantoins: A novel route to NHCs

Synthesis of polydithiourethanes and their thermal, optical, and mechanical properties originated from monomers structure

An unprecedented tandem 1,3-dipolar cycloaddition–cheletropic elimination: a facial approach to novel push–pull olefins

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