大学化学 >> 2023, Vol. 38 >> Issue (2): 192-196.doi: 10.3866/PKU.DXHX202204039

化学实验 上一篇    下一篇

三氟甲磺酸催化3, 5-二叔丁基对醌膦酸二苯酯串联环化反应——介绍一个有机化学综合实验

黄静, 孙胜男, 张瑞龙, 梁雨爽, 苗志伟()   

  • 收稿日期:2022-04-12 录用日期:2022-06-14 发布日期:2022-07-01
  • 通讯作者: 苗志伟 E-mail:miaozhiwei@nankai.edu.cn
  • 基金资助:
    国家自然科学基金(22071113);南开大学沧州渤海新区绿色化工研究院基金(NCC2020FH01)

Tandem Cyclization Reaction of Diphenyl 3, 5-Di-tert-butyl-p-quinone Phosphonate Catalyzed by Trifluoromethanesulfonic Acid: Introduce a Comprehensive Experiment of Organic Chemistry

Jing Huang, Shengnan Sun, Ruilong Zhang, Yushuang Liang, Zhiwei Miao()   

  • Received:2022-04-12 Accepted:2022-06-14 Published:2022-07-01
  • Contact: Zhiwei Miao E-mail:miaozhiwei@nankai.edu.cn

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摘要：

有机化合物的合成与结构表征是有机化学实验教学的重要内容。本文介绍一个有机化学综合实验，实验以3, 5-二叔丁基对醌膦酸二苯酯和2, 6-二羟基甲苯为反应物，在三氟甲磺酸催化下发生串联环化反应生成苯并[1,2]氧杂膦烷-2-氧化物，并利用核磁共振氢谱(1H NMR)、碳谱(13C NMR)、磷谱(31P NMR)和高分辨质谱(HRMS)对产物结构进行表征。

关键词: 有机化学综合实验, 串联环化反应, 苯并[1,2]氧杂膦烷-2-氧化物, 合成与结构表征

Abstract:

Synthesis and structural characterization of organic compounds are important content of organic chemistry laboratory teaching. This article introduces a comprehensive organic chemistry experiment carried out at College of Chemistry, Nankai University. In this experiment, diphenyl 3, 5-di-tert-butyl-p-quinone phosphonate and 2-methylbenzene-1, 3-diol are the reactants, and the tandem cyclization reaction occurred under the catalysis of trifluoromethanesulfonic acid to generate benzo[d] [1,2] oxaphosphole 2-oxide. The structure of the product is characterized by 1H NMR, 13C NMR, 13P NMR and HRMS.

Key words: Organic chemistry comprehensive experiment, Tandem cyclization reaction, Benzo[d] [1,2] oxaphosphole 2-oxide, Synthesis and structural characterization