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

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

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(^(1)H NMR)、碳谱(^(13)C NMR)、磷谱(^(31)P NMR)和高分辨质谱(HRMS)对产物结构进行表征。

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 ^(1)H NMR,^(13)C NMR,^(13)P NMR and HRMS.