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2021 , Vol. 41 >Issue 3: 947 - 958

DOI: https://doi.org/10.6023/cjoc202008046

综述与进展

氧杂环丁烷的扩环反应

  • 袁文豪 ,
  • 许家喜
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  • 1 北京化工大学化学学院有机化学系 化工资源有效利用国家重点实验室 北京 100029

收稿日期: 2020-08-25

  修回日期: 2020-09-22

  网络出版日期: 2020-10-15

基金资助

国家自然科学基金(21772010)

收起

Ring Expansions of Oxetanes

  • Wenhao Yuan ,
  • Jiaxi Xu
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  • 1 State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029
* Corresponding author. E-mail:

Received date: 2020-08-25

  Revised date: 2020-09-22

  Online published: 2020-10-15

Supported by

National Natural Science Foundation of China(21772010)

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摘要

氧杂环丁烷是一类重要的小杂环化合物, 也是重要有机合成中间体, 在有机化学、药物化学和高分子化学中都有广泛的应用. 作为具有较大环张力的小杂环化合物, 氧杂环丁烷类化合物除可以发生开环反应外, 也很容易发生扩环反应, 构建含氧普通环到大环化合物. 主要总结了氧杂环丁烷的扩环反应, 包括重氮化合物作为卡宾前体与氧杂环丁烷的扩环反应、金属催化的分子间环加成和邻基参与的分子内环加成反应及亲核扩环反应等. 分析了一些扩环反应的机理, 并对扩环反应未来的发展提出了新的展望.

关键词： 氧杂环丁烷; 扩环; 卡宾; 环加成; 亲核反应

本文引用格式

袁文豪 , 许家喜 . 氧杂环丁烷的扩环反应[J]. 有机化学, 2021 , 41(3) : 947 -958 . DOI: 10.6023/cjoc202008046

Abstract

Oxetanes are a class of important small heterocycles and intermediates in organic synthesis and have been widely applied in organic, pharmaceutical and polymer chemistries. As small heterocycles with a large ring tension, oxetanes not only prefer ring-opening reactions, but also favor ring expansions, to construct oxygen-containing common to large heterocyclic compounds. The ring expansion reactions of oxetanes, including the ring expansions with diazo compounds as carbene precursors, the metal catalyzed intermolecular cycloadditions and the intramolecular cycloadditions involving neighboring group participation, the nucleophilic ring expansion and so on are reviewed. Some reaction mechanisms of ring expansion reactions are analyzed, and new prospects for the future development of the ring expansion reactions are put forward.

Key words： oxetane; ring expansion; carbene; cycloaddition; nucleophilic reaction

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