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Investigation into thiol-(meth)acrylate Michael addition reactions using amine and phosphine catalysts
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Li, Guang-Zhao, Randev, Rajan, Soeriyadi, Alexander H., Rees, Gregory J., Boyer, Cyrille, Tong, Zhen, Davis, Thomas P., Becer, C. Remzi and Haddleton, David M. (2010) Investigation into thiol-(meth)acrylate Michael addition reactions using amine and phosphine catalysts. Polymer Chemistry, Vol.1 (No.8). pp. 1196-1204. doi:10.1039/c0py00100g
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Official URL: http://dx.doi.org/10.1039/c0py00100g
Abstract
This work describes a study into thiol-ene based Michael addition reactions. Different catalysts, primary and tertiary amines and phosphines, were investigated for the reaction of a range of thiols with dimers and oligomers of some (meth)acrylates. Primary and tertiary amines are efficient catalysts for the thiol-ene reaction, although these catalysts require several hours to reach high conversion. Moreover, the phosphine catalysts, dimethylphenylphosphine (DMPP) and tris-(2-carboxyethyl)phosphine (TCEP), were investigated in detail. DMPP is an efficacious catalyst yielding complete conversion in few minutes under optimized conditions. Importantly, the concentration of DMPP should be kept at catalytic levels to avoid the formation of by-products, originating from the addition of DMPP to the vinyl group. Furthermore, TCEP is an efficient catalyst for thiol-ene reactions in aqueous media when the pH of the medium is higher than 8.0 since at acidic pH the formation of by-products is observed.
| Item Type: | Journal Article | ||||
|---|---|---|---|---|---|
| Subjects: | Q Science > QD Chemistry | ||||
| Divisions: | Faculty of Science > Chemistry | ||||
| Library of Congress Subject Headings (LCSH): | Polymerization, Thiols, Addition reactions, Methyl methacrylate, Polymers, Butyl methacrylate | ||||
| Journal or Publication Title: | Polymer Chemistry | ||||
| Publisher: | Royal Society of Chemistry | ||||
| ISSN: | 1759-9954 | ||||
| Official Date: | October 2010 | ||||
| Dates: |
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| Volume: | Vol.1 | ||||
| Number: | No.8 | ||||
| Number of Pages: | 9 | ||||
| Page Range: | pp. 1196-1204 | ||||
| DOI: | 10.1039/c0py00100g | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access | ||||
| Funder: | China Scholar Council (CSC), Australian Research Council (ARC), European Union (EU), Advantage West Midlands (AWM), European Regional Development Fund (ERDF) | ||||
| Grant number: | 235999 (EU) |
Data sourced from Thomson Reuters' Web of Knowledge
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