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Organocatalytic selective coupling of episulfides with carbon disulfide for the synthesis of poly(trithiocarbonate)s and cyclic trithiocarbonates
Polymer Chemistry ( IF 4.1 ) Pub Date : 2022-05-26 , DOI: 10.1039/d2py00405d Chao Chen 1 , Yves Gnanou 1 , Xiaoshuang Feng 1
Polymer Chemistry ( IF 4.1 ) Pub Date : 2022-05-26 , DOI: 10.1039/d2py00405d Chao Chen 1 , Yves Gnanou 1 , Xiaoshuang Feng 1
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This work reports how to efficiently utilize carbon disulfide (CS2) as a sulfur-containing C1 resource for the purpose of synthesizing both linear poly(trithiocarbonate)s and cyclic trithiocarbonates. When initiated by PPNCl or phosphazene benzoxide, the copolymerization of CS2 with episulfides affords perfectly alternating poly(trithiocarbonate)s in the absence of any catalyst. In contrast, when initiated by tetrabutylammonium halide, the same coupling reaction of CS2 with episulfides results in the formation of cyclic trithiocarbonates. The role played by initiating onium salts in the linear/cyclic selectivity as well as reaction conditions such as the temperature, the type of solvent, and the feeding ratio of CS2 to episulfides was investigated. Lastly, when placed in the presence of a radical source or treated with UV irradiation, poly(trithiocarbonate)s undergo complete unzipping to produce cyclic trithiocarbonates. This remarkable feature has been harnessed to prepare degradable polymers using oligotrithiocarbonates as self-immolating linkers between dithiol alkyl precursors.
中文翻译：
环硫化物与二硫化碳的有机催化选择性偶联合成聚（三硫代碳酸酯）和环状三硫代碳酸酯
这项工作报告了如何有效地利用二硫化碳 (CS 2 ) 作为含硫 C1 资源来合成线性聚三硫代碳酸酯和环状三硫代碳酸酯。当由 PPNCl 或苯氧化磷腈引发时，CS 2与环硫化物的共聚在没有任何催化剂的情况下提供了完美交替的聚（三硫代碳酸酯）。相反，当由卤化四丁基铵引发时，CS 2与环硫化物的相同偶联反应导致形成环状三硫代碳酸酯。引发鎓盐对线性/环状选择性以及反应温度、溶剂种类、CS 2投料比等反应条件的影响对环硫化物进行了研究。最后，当放置在自由基源的存在下或用紫外线照射处理时，聚（三硫代碳酸酯）经历完全解链以产生环状三硫代碳酸酯。这一显着特征已被用于使用低聚三硫代碳酸酯作为二硫醇烷基前体之间的自牺牲连接体来制备可降解聚合物。
更新日期：2022-05-26
中文翻译：
环硫化物与二硫化碳的有机催化选择性偶联合成聚（三硫代碳酸酯）和环状三硫代碳酸酯
这项工作报告了如何有效地利用二硫化碳 (CS 2 ) 作为含硫 C1 资源来合成线性聚三硫代碳酸酯和环状三硫代碳酸酯。当由 PPNCl 或苯氧化磷腈引发时，CS 2与环硫化物的共聚在没有任何催化剂的情况下提供了完美交替的聚（三硫代碳酸酯）。相反，当由卤化四丁基铵引发时，CS 2与环硫化物的相同偶联反应导致形成环状三硫代碳酸酯。引发鎓盐对线性/环状选择性以及反应温度、溶剂种类、CS 2投料比等反应条件的影响对环硫化物进行了研究。最后，当放置在自由基源的存在下或用紫外线照射处理时，聚（三硫代碳酸酯）经历完全解链以产生环状三硫代碳酸酯。这一显着特征已被用于使用低聚三硫代碳酸酯作为二硫醇烷基前体之间的自牺牲连接体来制备可降解聚合物。
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