trans-2-(2-Methoxyphenyl)-5-oxotetrahydrofuran-3-carboxylic acid
CAS Number:
99226-02-5
Molecular Formula:
C12H12O5
Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification
Literature Information
Publication Date
2014-07-16
DOI
10.1039/C4PY00783B
Impact Factor
5.582
Authors
Taylor W. Gaines, Kenneth B. Wagener, Robert P. Burford, Andrew B. Lowe
View Original
Abstract
The synthesis of the novel α,ω-diene 2-(undec-10-en-1-yl)tridec-12-en-1-yl acrylate is described. Thiol-Michael coupling of this substrate followed by chemoselective oxidation of the thioether moiety with triazotriphosphorine tetrachloride (TAPC) furnished a suite of functional and symmetrical ADMET-active monomers in a quick and convenient manner. Polymerization of these adducts with Grubbs 1st generation catalyst (RuCl2(PCy3)2CHPh) was demonstrated to high conversion, and quantitative radical initiated thiol–ene modification of the backbone CC bonds was performed to impart additional functionality to each ADMET polymer. These reactions highlight the compatibility of thiol-based click chemistries for the preparation and post-modification of functional ADMET materials.
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Source Journal
Polymer Chemistry
CiteScore:
8.6
Self-citation Rate:
7.3%
Articles per Year:
457
Polymer Chemistry welcomes submissions in all areas of polymer science that have a strong focus on macromolecular chemistry. Manuscripts may cover a broad range of fields, yet no direct application focus is required.
Recommended Compounds
![[4-Chloro-3-(diethylcarbamoyl)phenyl]boronic acid structure](https://static.chemtradehub.com/structs/871/871332-68-2-0e3b.webp "[4-Chloro-3-(diethylcarbamoyl)phenyl]boronic acid structure")
[4-Chloro-3-(diethylcarbamoyl)phenyl]boronic acid
CAS Number:
871332-68-2
Molecular Formula:
C11H15BClNO3
Benzyl 3-(aminomethyl)piperidine-1-carboxylate hydrochloride
CAS Number:
1186663-23-9
Molecular Formula:
C14H21ClN2O2
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