Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification

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发布日期 2014-07-16

DOI 10.1039/C4PY00783B

影响因子 5.582

作者

Taylor W. Gaines, Kenneth B. Wagener, Robert P. Burford, Andrew B. Lowe

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摘要

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.

期刊推荐

Chemistry of Natural Compounds

Bulletin of the Chemical Society of Japan

Accounts of Chemical Research

Australian Journal of Chemistry

AIAA Journal

Anti-Corrosion Methods and Materials

Chemistry of Heterocyclic Compounds

Corrosion Science

Advances in Colloid and Interface Science

Chemical Reviews

来源期刊

Polymer Chemistry

CiteScore: 8.6

自引率: 7.3%

年发文量: 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.

Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification

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Polymer Chemistry

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