多面体低聚八(二苯砜基)硅倍半氧烷合成优化及磺酰化机理研究
收稿日期: 2014-05-13
修回日期: 2014-07-06
网络出版日期: 2014-07-15
基金资助
国家自然科学基金(No.512730223)资助项目.
Optimal Synthesis and Sulfonylation Mechanism of a Novel Polyhedral Oligomeric Octadiphenylsulfonylsilsesquioxane
Received date: 2014-05-13
Revised date: 2014-07-06
Online published: 2014-07-15
Supported by
Project supported by the National Natural Science Foundation of China (No.512730223).
以笼型低聚八苯基硅倍半氧烷(OPS)为原料, AlCl3为催化剂, 苯磺酰氯为磺酰化试剂, 在二氯甲烷溶液中反应72h, 合成了笼型八(二苯砜基)硅倍半氧烷(ODPSS). 该方法合成过程简单稳定, 产率高. 通过FTIR、MALDI-TOF MS、1H NMR、13C NMR、29Si NMR和元素分析对产物进行了表征, 证明OPS已完全转化为ODPSS. 通过改变溶剂、催化剂、反应时间和各反应物物质的量之比, 优化了反应条件, 分析了反应机理, 建立了该体系下OPS的磺酰化反应机理模型.
关键词： 八(二苯砜基)硅倍半氧烷; 傅-克磺酰化; 八苯基硅倍半氧烷
李紫千 , 杨荣杰 . 多面体低聚八(二苯砜基)硅倍半氧烷合成优化及磺酰化机理研究[J]. 有机化学, 2014 , 34(11) : 2338 -2344 . DOI: 10.6023/cjoc201405022
Octadiphenylsulfonylsilsesquioxane (ODPSS) was synthesized through sulfonylation of octaphenylsilsesquioxane (OPS) with benzenesulfonyl chloride and the AlCl3 catalyst in dichloromethane (CH2Cl2). By changing the solvent, catalyst, reaction time and molar ratio of reactants, the optimal reaction conditions were determined. It was found that OPS could be completely converted to ODPSS with a high yield. The product ODPSS was identified by FTIR, MALDI-TOF MS, 1H NMR, 13C NMR, 29Si NMR and elemental analysis. The reaction mechanism was analyzed and a sulfonylation model of OPS was established.
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