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

被引：18

作者：

van Hensbergen, Johannes A. ^{[1
,2
,3
]}

Gaines, Taylor W. ^{[2
,3
]}

Wagener, Kenneth B. ^{[2
,3
]}

Burford, Robert P. ^{[1
]}

Lowe, Andrew B. ^{[1
]}

机构：

[1] UNSW Australia, Ctr Adv Macromol Design, Sch Chem Engn, Sydney, NSW 2052, Australia

[2] Univ Florida, Dept Chem, George & Josephine Butler Polymer Res Lab, Gainesville, FL 32611 USA

[3] Univ Florida, Ctr Macromol Sci & Engn, Gainesville, FL 32611 USA

来源：

POLYMER CHEMISTRY | 2014年 / 5卷 / 21期

基金：

澳大利亚研究理事会; 美国国家科学基金会;

关键词：

OLEFIN METATHESIS; CLICK CHEMISTRY; RENEWABLE RESOURCES; FACILE ACCESS; PV-OLIGOMERS; HETERO-DIELS; ACID; COPOLYMERS; RAFT; POLYETHYLENE;

D O I：

10.1039/c4py00783b

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

The synthesis of the novel alpha,omega-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)(2)CHPh) was demonstrated to high conversion, and quantitative radical initiated thiolene modification of the backbone C = C 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.

引用

页码：6225 / 6235

页数：11

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