Chirality induction in cyclocopolymerization. 13. Structural effect of 1,3-diol as chiral templates in the cyclocopolymerization of bis(4-vinylbenzoate)s with styrene
Chirality induction in cyclocopolymerization. 13. Structural effect of 1,3-diol as chiral templates in the cyclocopolymerization of bis(4-vinylbenzoate)s with styrene
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DOI：
10.1021/ma000097
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发表时间：
2000-05-30
期刊：
影响因子：
5.5
通讯作者：
Yokota, K
中科院分区：
文献类型：
--
作者：
Kakuchi, T;Narumi, A;Yokota, K
以(1S,2R)-2-羟甲基-1-环己醇(a)和(1S,2S)-2-羟甲基-1-环己醇(bi)等两种非对映手性环烷二醇为(S)-1,3-丁二醇(c)的构象限制模型，作为手性模板，研究了模板部分的1,3-二醇骨架的构象效应。双(4-乙烯基苯甲酸酯) (1) 与苯乙烯的环共聚反应得到的无模板聚合物 3a 的比旋光度几乎是 3b 的两倍。与手性模板 c 相比，手性诱导的效率按 b < c < a 的顺序增加。
Two diastereomeric chiral cycloalkanediols such as (1S,2R)-2-hydroxymethyl-1-cyclohexanol (a) and (1S,2S)-2-hydroxymethyl-1-cyclohexanol (bi, which were conformational restriction models for (S)-1,3-butanediol (c), were used as chiral templates tu investigate the conformational effect uf the 1,3-diol skeleton of the template moiety in the cyclocopolymerization of bis(4-vinylbenzoate)s (1) with styrene. The specific rotation for the resulting template-free polymer 3a was almost twice that for 3b. In comparison with chiral template c, the efficiency of the chirality induction increases in the order of b < c < a. These characteristics of chiral templates were discussed in terms of the conformational distribution of the monomer 1a-c.