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Synthesis,Characterization, Polymerization of Optically Active Terminal Epoxides and Episulfides Bearing Bulky Groups |
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| Authors: | SUN Yun-kai ZHANG Jin LIU Hui-jun HE Li GONG Hang YANG Nian-fa |
| Affiliation: | 1. Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. China; 2. School of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, P. R. China |
| Abstract: | A simple and efficient protocol was developed for the syntheses of optically active epoxides(2a-2d) via the reactions of epichlorohydrin with organometallic reagents with steric hindrance at low temperature. On this basis, episulfides(3a-3d) were obtained with high e.e. values by the reaction of the corresponding epoxides with NH4SCN. The configuration of thiiranes was opposite to that of the corresponding epoxides. Then, epoxides 2a-2d were anionically polymerized and the poly-R-2a(or poly-S-2a) was proved to keep a stable one-handed helical conformation in solution. The oligomers[degree of polymerization(DP)=2-5] were obtained when the thiiranes(3a, 3b and 3c) were used to polymerize. |
| Keywords: | Optical activity Epoxide Episulfide One-handed helicity |
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