Anionic ring-opening polymerization of a five-membered cyclic urethane derived from d-glucosamine,Journal of Polymer Science Part A: Polymer Chemistry

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Anionic ring-opening polymerization of a five-membered cyclic urethane derived from d-glucosamine
Journal of Polymer Science Part A: Polymer Chemistry Pub Date : 2019-10-11 , DOI: 10.1002/pola.29511
Osamu Haba ₁ , Yosuke Akashika ₁

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The anionic ring-opening polymerization of a five-membered cyclic urethane, 2-amino-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-α,d-glucopyranoside (MBUG), which was prepared from naturally abundant d-glucosamine, was examined. Potassium tert-butoxide (t-BuOK) was the most effective initiator among the evaluated bases and produced polyurethane with the Mn of 7800 without any elimination of CO₂. The equimolar reaction of MBUG and t-BuOK in the presence of CH₃I produced N-methylated MBUG and suggested that the initiation reaction involves proton abstraction from the NH group. This N-methylated compound did not undergo the polymerization. Therefore, the mechanism of propagation in the ROP of MBUG should involve the proton abstraction and nucleophilic substitution of the resulting amide anion. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2491–2497

中文翻译：

d-氨基葡萄糖衍生的五元环状氨基甲酸酯的阴离子开环聚合

五元环状氨基甲酸酯、2-氨基-4,6-O-亚苄基-2- N ,3 - O-羰基-2-脱氧-α, d-吡喃葡萄糖苷( MBUG )的阴离子开环聚合反应由天然丰富的d-氨基葡萄糖制备，进行了检查。叔丁醇钾(t-BuOK) 是评估的碱中最有效的引发剂，它生产的聚氨酯的 Mn 为 7800，没有任何 CO ₂消除。_{在 CH 3} I存在下 MBUG 和 t-BuOK 的等摩尔反应产生了N-甲基化 MBUG，这表明引发反应涉及从 NH 基团夺取质子。这N-甲基化的化合物不发生聚合。因此，MBUG 在 ROP 中的传播机制应该涉及质子提取和所得酰胺阴离子的亲核取代。© 2019 Wiley Periodicals, Inc. J. Polym。科学，A 部分：Polym。化学。2019 , 57 , 2491–2497

更新日期：2019-10-11

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