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Trends in the Diels–Alder reaction in polymer chemistry
Chemical Society Reviews ( IF 40.4 ) Pub Date : 2021-08-17 , DOI: 10.1039/d0cs01382j
Benoit Briou 1 , Bruno Améduri 1 , Bernard Boutevin 1
Affiliation  

The Diels–Alder (DA) reaction is regarded as quite a useful strategy in organic and macromolecular syntheses. The reversibility of this reaction and the advent of self-repair technology, as well as other applications in controlled macromolecular architectures and crosslinking, have strongly boosted the research activity, which is still attracting a huge interest in both academic and industrial research. The DA reaction is a simple and scalable toolbox. Though it is well-established that furan/maleimide is the most studied diene/dienophile couple, this perspective article reports strategies using other reversible systems with deeper features on other types of diene/dienophile pairs being either petro-sourced (cyclopentadiene, anthracene) or bio-sourced (muconic and sorbic acids, myrcene and farnesene derivatives, eugenol, cardanol). This review is composed of four sections. The first one briefly recalls the background on the DA reactions involving cyclodimerizations, dienes, and dienophiles, parameters affecting the reaction, while the second part deals with the furan/maleimide reaction. The third one deals with petro-sourced and bio-sourced (or products becoming bio-sourced) reactants involved in DA reactions are also listed and discussed. Finally, the authors’ opinion is given on the potential future of the crosslinking–decrosslinking reaction, especially regarding the process (e.g., key temperatures of decrosslinking) or possibly monocomponents. It presents both fundamental and applied research on the DA reaction and its applications.

中文翻译:

高分子化学中 Diels-Alder 反应的趋势

Diels-Alder (DA) 反应被认为是有机和大分子合成中非常有用的策略。该反应的可逆性和自修复技术的出现,以及在可控大分子结构和交联中的其他应用,极大地促进了研究活动,这仍然引起了学术和工业研究的巨大兴趣。DA 反应是一个简单且可扩展的工具箱。尽管呋喃/马来酰亚胺是研究最多的二烯/亲二烯对,但这篇观点文章报告了使用其他可逆系统的策略,这些系统对其他类型的二烯/亲二烯对具有更深层次的特征,这些对是石油来源的(环戊二烯、蒽)或生物来源(粘康酸和山梨酸、月桂烯和法呢烯衍生物、丁香酚、腰果酚)。本综述由四个部分组成。第一部分简要回顾了涉及环二聚、二烯和亲二烯体的 DA 反应的背景、影响反应的参数,而第二部分则涉及呋喃/马来酰亚胺反应。第三个涉及 DA 反应中涉及的石油来源和生物来源(或成为生物来源的产品)反应物也被列出和讨论。最后,作者对交联-解交联反应的潜在未来给出了意见,特别是关于该过程(第三个涉及 DA 反应中涉及的石油来源和生物来源(或成为生物来源的产品)反应物也被列出和讨论。最后,作者对交联-解交联反应的潜在未来给出了意见,特别是关于该过程(第三个涉及 DA 反应中涉及的石油来源和生物来源(或成为生物来源的产品)反应物也被列出和讨论。最后,作者对交联-解交联反应的潜在未来给出了意见,特别是关于该过程(例如,解交联的关键温度)或可能的单组分。它介绍了 DA 反应及其应用的基础和应用研究。
更新日期:2021-08-17
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