Introducing Multicomponent Reactions to Polymer Science: Passerini Reactions of Renewable Monomers

Introducing Multicomponent Reactions to Polymer Science: Passerini Reactions of Renewable Monomers
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DOI:
10.1021/ja1113003
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发表时间:
2011-02-16
影响因子:
15
通讯作者:
Meier, Michael A. R.
Meier, Michael A. R.
中科院分区:
化学1区
文献类型:
--
作者:
Kreye, Oliver;Toth, Tommy;Meier, Michael A. R.

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Passerini三组分反应(3CR)和烯烃复分解的组合导致聚[1-(烷基氨基甲酰基)烷基链烷酸酯]的形成,这是一类在其侧链中具有酰胺部分的新型聚酯,来自可再生资源。两种不同的方法进行了研究和相互比较。首先,通过Passerini-3CR合成单体,然后通过无环二烯复分解聚合。或者,通过自复分解合成双官能单体,然后通过Passerini-3CR聚合。这两种方法都导致了高分子量聚合物的形成。此外,Passerini-3CR被证明是一种通用的移植方法。结果清楚地表明,Passerini-3CR为单体和聚合物提供了一种有趣的新途径,从而拓宽了聚合物科学的合成组合。
Combination of the Passerini three component-reaction (3CR) and olefin metathesis led to the formation of poly[1-(alkyl carbamoyl)alkyl alkanoates], a new class of polyesters with amide moieties in their side chain, from renewable resources. Two different approaches were studied and compared to each other. First, monomers were synthesized by the Passerini-3CR and then polymerized via acyclic diene metathesis. Alternatively, bifunctional monomers were synthesized by self-metathesis and then polymerized by Passerini-3CR. Both approaches led to the formation of high-molecular-weight polymers. Moreover, Passerini-3CRs were shown to be a versatile grafting-onto method. The results clearly demonstrate that the Passerini-3CR offers an interesting new access to monomers and polymers and thus broadens the synthetic portfolio of polymer science.