A facile and Convenient Method for Synthesis of Thiiranes under Mild Condition Using Phase Transfer Catalyst

Gholami, Maryam; Afshari, Mozhgan

doi:10.13005/ojc/290454

Cited by 4 publications

(2 citation statements)

References 7 publications

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“…Besides, the high oxidative responsivity and hydrophobicity of polythioethers make them promising hydrophobic segments for oxidation-responsive nanocontainers. , Hence, we examined the ability of AMCs to promote the ROP of episulfides. Different kinds of episulfide were synthesized in accordance with reported method, and the products were characterized by 1 H and 13 C NMR spectra (Figures S32–S37). The ROP of 2-(ethoxymethyl)thiirane (EMT) was performed with PET as the initiator and cesium pivalate as the catalyst at room temperature.…”

Section: Resultsmentioning

confidence: 99%

Polyether/Polythioether Synthesis via Ring-Opening Polymerization of Epoxides and Episulfides Catalyzed by Alkali Metal Carboxylates

et al. 2022

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Alkali metal carboxylates were evaluated as simple and green catalysts for the ring-opening polymerization (ROP) of various epoxides (e.g., alkyl-substituted epoxides and glycidyl ethers) and episulfides (alkyl-substituted episulfides and thioglycidyl ethers). The thus-produced functional polyethers (end-functionalized polyethers, block copolyethers, polyether–polyester block copolymers, topologically unique polyethers, and isotactic-enriched polyethers) and polythioethers featured well-defined structures and controlled molecular weights (M n,SEC = 1.0–32 kg mol–1). The most effective catalyst was identified as cesium pivalate, and the variation of carboxylate moieties and alkali metal cations enabled the tuning of acid/base characteristics and thus allowed one to control polymerization behavior and expand the scope of functional monomers and initiators. Kinetic analysis confirmed the controlled/living nature of the polymerization process, while mechanistic studies revealed that carboxylate moieties did not directly initiate the ring-opening of epoxide monomers via nucleophilic attack but rather activated the alcohol initiators/chain ends via H-bonding and thus rendered the corresponding OH groups sufficiently nucleophilic to attack the alkali metal cation-activated epoxides.

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Section: Resultsmentioning

confidence: 99%

Polyether/Polythioether Synthesis via Ring-Opening Polymerization of Epoxides and Episulfides Catalyzed by Alkali Metal Carboxylates

et al. 2022

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“…Also, epoxides can be converted to thiiranes in reaction with different sulfur donor reagents such as thiourea, dimethylthioformamide, inorganic thiocyanates, phosphine sulfide and 3‐methylbenzothiazol‐2‐thione . Often these reactions take place in the presence of various acidic or basic catalysts . Thiiranes as important precursors have been also used for various purposes …”

Section: Introductionmentioning

confidence: 99%

[Fe₃O₄@SiO₂@(CH₂)₃im]C₆F₅O as a New Hydrophilic and Task‐Specific Nanomagnetic Catalyst: Application for Synthesis of β‐Azido Alcohols and Thiiranes under Mild and Green Conditions

2018

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[Fe3O4@SiO2@(CH2)3im]C6F5O was designed, synthesized and characterized by various techniques such as Fourier transform spectroscopy infrared (FT‐IR), X‐ray diffraction patterns (XRD), Field scanning electron microscopy (FESEM), transmission electron microscopy (TEM), energy‐dispersive X‐ray spectroscopy (EDX) and vibrating sample magnetometer (VSM). The described novel hydrophilic nanomagnetic particles were applied as an efficient and reusable catalyst in the ring opening of epoxides using sodium azide for the preparation of β‐azido alcohols. Conversion of epoxides to their thiiranes in water by using potassium thiocyanate in the presence of a catalytic amount of mentioned nanomagnetic catalyst was also carried out.

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Thiiranes and Thiirenes: Monocyclic

Plażuk

Łomzik

Chrabąszcz

et al. 2022

Comprehensive Heterocyclic Chemistry IV

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A facile and Convenient Method for Synthesis of Thiiranes under Mild Condition Using Phase Transfer Catalyst

Abstract: A mild and efficient process for preparation of thiiranes with KSCN in water at room temperature using a catalytic amount of 1,4-bis(triphenylphosphonium)-2-butene dichloride is described.

Cited by 4 publications

References 7 publications

Polyether/Polythioether Synthesis via Ring-Opening Polymerization of Epoxides and Episulfides Catalyzed by Alkali Metal Carboxylates

Polyether/Polythioether Synthesis via Ring-Opening Polymerization of Epoxides and Episulfides Catalyzed by Alkali Metal Carboxylates

[Fe₃O₄@SiO₂@(CH₂)₃im]C₆F₅O as a New Hydrophilic and Task‐Specific Nanomagnetic Catalyst: Application for Synthesis of β‐Azido Alcohols and Thiiranes under Mild and Green Conditions

Thiiranes and Thiirenes: Monocyclic

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A facile and Convenient Method for Synthesis of Thiiranes under Mild Condition Using Phase Transfer Catalyst

Abstract: A mild and efficient process for preparation of thiiranes with KSCN in water at room temperature using a catalytic amount of 1,4-bis(triphenylphosphonium)-2-butene dichloride is described.

Cited by 4 publications

References 7 publications

Polyether/Polythioether Synthesis via Ring-Opening Polymerization of Epoxides and Episulfides Catalyzed by Alkali Metal Carboxylates

Polyether/Polythioether Synthesis via Ring-Opening Polymerization of Epoxides and Episulfides Catalyzed by Alkali Metal Carboxylates

[Fe3O4@SiO2@(CH2)3im]C6F5O as a New Hydrophilic and Task‐Specific Nanomagnetic Catalyst: Application for Synthesis of β‐Azido Alcohols and Thiiranes under Mild and Green Conditions

Thiiranes and Thiirenes: Monocyclic

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[Fe₃O₄@SiO₂@(CH₂)₃im]C₆F₅O as a New Hydrophilic and Task‐Specific Nanomagnetic Catalyst: Application for Synthesis of β‐Azido Alcohols and Thiiranes under Mild and Green Conditions