Abstract Levoglucosenone (LGO) is a cellulose-derived and commercially available platform molecule that is produced at an industrial scale. LGO contains a highly reactive double bond that was used to produce two isomers of norbornene-containing LGO monomers, endo-N-LGO (1) and exo-N-LGO (2). Furthermore, Baeyer-Villiger oxidation of 1 was performed to yield a highly-valuable chiral monomer, endo-N-HBO (3). The norbornene moiety of the prepared monomers was readily polymerized by ring-opening metathesis polymerization (ROMP) in the presence of GI catalyst to access highly thermostable polymers with Td5% up to 360 °C in the case of N-LGO-based polymers and Td5% in the range of 374–380 °C when 3 was polymerized, such range of Td5% being the highest reported up-to-date for the LGO-derived polymers. The effect of monomer concentration over the polymerization process was studied and showed that 4 M solutions lead to a better monomer conversion while preserving the control over the polymer structure and reducing the environmental factor (E factor). GI was found active in the ROMP of 3 without the need of protecting the hydroxy group and thus leading to pendent hydroxy functional polymers. Furthermore, for the first time, copolymers containing both LGO and HBO reactive moieties were prepared by random copolymerization of 1 and 3.

中文翻译：

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通过左旋葡萄糖酮衍生单体的开环复分解聚合直接获得后功能化聚合物

摘要 Levoglucosenone (LGO) 是一种纤维素衍生的可商业化平台分子，以工业规模生产。LGO 含有一个高反应性双键，用于生产含降冰片烯的 LGO 单体的两种异构体，即内型-N-LGO (1) 和外型-N-LGO (2)。此外，对 1 进行 Baeyer-Villiger 氧化以产生高价值的手性单体，endo-N-HBO (3)。所制备单体的降冰片烯部分在 GI 催化剂的存在下通过开环复分解聚合 (ROMP) 容易地聚合，以在 N-LGO 基聚合物和 Td5 的情况下获得 Td5% 高达 360°C 的高热稳定性聚合物当 3 聚合时，Td5% 的范围在 374-380 °C 范围内，这样的 Td5% 范围是迄今为止报道的 LGO 衍生聚合物的最高值。研究了单体浓度对聚合过程的影响，结果表明 4 M 溶液可实现更好的单体转化，同时保持对聚合物结构的控制并减少环境因素（E 因子）。发现 GI 在 3 的 ROMP 中具有活性，而无需保护羟基，从而产生悬垂的羟基官能聚合物。此外，首次通过 1 和 3 的无规共聚制备了同时含有 LGO 和 HBO 反应性部分的共聚物。发现 GI 在 3 的 ROMP 中具有活性，而无需保护羟基，从而产生悬垂的羟基官能聚合物。此外，首次通过 1 和 3 的无规共聚制备了同时含有 LGO 和 HBO 反应性部分的共聚物。发现 GI 在 3 的 ROMP 中具有活性，而无需保护羟基，从而产生悬垂的羟基官能聚合物。此外，首次通过 1 和 3 的无规共聚制备了同时含有 LGO 和 HBO 反应性部分的共聚物。