LiOH-Catalyzed Simple Ring Opening of Epoxides Under Solvent-Free Conditions

Azizi, Najmedin; Khajeh‐Amiri, Alireza; Ghafuri, Hossein; Bolourtchian, Mohammad

doi:10.1080/10426500903127573

Cited by 17 publications

(11 citation statements)

References 41 publications

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“…Finally, lithium hydroxide (LiOH) was employed as the reaction catalyst and aqueous THF (10% water) was used as the reaction medium. 69 In this case, at the catalyst loading of 1.2 mol% and a reaction time of 1 hour, 90% conversion was achieved (Table 2 and Fig. 5).…”

Section: First Functionalization Through the Thiol-epoxy Reactionmentioning

confidence: 74%

Homopolymer bifunctionalization through sequential thiol–epoxy and esterification reactions: an optimization, quantification, and structural elucidation study

2015

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Section: First Functionalization Through the Thiol-epoxy Reactionmentioning

confidence: 74%

Homopolymer bifunctionalization through sequential thiol–epoxy and esterification reactions: an optimization, quantification, and structural elucidation study

2015

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“…Therefore, lithium hydroxide was used as the polymerization catalyst. This catalyst has been used with significant success for the thiol‐epoxy coupling reaction in small molecular as well as polymeric (a–c) systems. This reaction produced a relatively higher molecular weight polymer ( M w = 28,500, M n = 15,900 g/mol).…”

Section: Resultsmentioning

confidence: 99%

Thiol‐epoxy polymerization via an AB monomer: Synthetic access to high molecular weight poly(β‐hydroxythio‐ether)s

Binder

Gadwal

Bielmann

et al. 2014

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

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A synthetic route is developed for the preparation of an AB-type of monomer carrying an epoxy and a thiol group. Base-catalyzed thiol-epoxy polymerization of this monomer gave rise to poly(b-hydroxythio-ether)s. A systematic variation in the reaction conditions suggested that tetrabutyl ammonium fluoride, lithium hydroxide, and 1,8-diazabicycloundecene (DBU) were good polymerization catalysts. Triethylamine, in contrast, required higher temperatures and excess amounts to yield polymers. THF and water could be used as polymerization mediums. However, the best results were obtained in bulk conditions. This required the use of a mechanical stirrer due to the high viscosity of the polymerization mixture. The polymers obtained from the AB monomer route exhibited significantly higher molecular weights (M w 5 47,700, M n 5 23,200 g/mol) than the materials prepared from an AA/BB type of the monomer system (M w 5 10,000, M n 5 5400 g/mol). The prepared reactive polymers could be transformed into a fluorescent or a cationic structure through postpolymerization modification of the reactive hydroxyl sites present along the polymer backbone.

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“…This process is known to be simple, modular, regio‐selective, robust, and high yielding. Hence, it is used widely in generation of small molecules as well as crosslinked thin films and bulk materials . Of late, the focus is slowly turning toward harnessing many attributes of this process for the preparation of well‐defined polymers and for post‐polymerization modification purposes.…”

Section: Introductionmentioning

confidence: 99%

Thiol‐epoxy “click” chemistry: Application in preparation and postpolymerization modification of polymers

Stuparu

Khan

2016

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

128

104

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Base-catalyzed reaction between a thiol and an epoxide group is a simple fusion process that leads to the formation of a b-hydroxythio-ether linkage. This reaction is efficient, regio-selective, and fast. In addition, it produces a reactive hydroxyl group upon completion. Therefore, it is of considerable potential in synthesis of reactive and functional soft materials. Here, we discuss the fundamental aspects of this process, the so-called thiol-epoxy "click" reaction, and its utility in the preparation and post-polymerization functionaliza-tion of polymers and crosslinked networks. Furthermore, its application in surface modification of solid substrates is also considered. Finally, utility of multifunctional materials created using the thiol-epoxy reaction is discussed in the biomedical arena.

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LiOH-Catalyzed Simple Ring Opening of Epoxides Under Solvent-Free Conditions

Cited by 17 publications

References 41 publications

Homopolymer bifunctionalization through sequential thiol–epoxy and esterification reactions: an optimization, quantification, and structural elucidation study

Homopolymer bifunctionalization through sequential thiol–epoxy and esterification reactions: an optimization, quantification, and structural elucidation study

Thiol‐epoxy polymerization via an AB monomer: Synthetic access to high molecular weight poly(β‐hydroxythio‐ether)s

Thiol‐epoxy “click” chemistry: Application in preparation and postpolymerization modification of polymers

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