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Citation: Jiaxin Wang, Zichun Li, Yuanying Dou, Xulang Chen. Synthesis of Triphenylene Derivatives: Introducing the Formation of Benzene Rings into the Experimental Teaching of Organic Chemistry[J]. University Chemistry, ;2023, 38(4): 331-335. doi: 10.3866/PKU.DXHX202210038 shu

Synthesis of Triphenylene Derivatives: Introducing the Formation of Benzene Rings into the Experimental Teaching of Organic Chemistry

College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002, Hubei Province, China

Corresponding author: Xulang Chen, xulangchen@hbnu.edu.cn
Received Date: 12 October 2022

In this study, the research hotspot of polycyclic aromatic hydrocarbons was introduced into undergraduate experimental teaching, and a synthesis experiment based on the aldol and Diels-Alder reactions was developed for benzene ring formation. Using 9,10-phenanthrenequinone and dibenzyl ketone as raw materials, the cyclopentadienone derivative 1 was obtained by the aldol reaction, and 1 was further reacted with diethyl acetylene dicarboxylate to obtain triphenylene derivative 2 by the Diels-Alder reaction. The reagents in this study are easily accessible, the reaction conditions are mild, the phenomenon is clear, the purification is simple, and the reliability is high. Students can master the principle and operation of the aldol and Diels-Alder reactions and gain an understanding of the important strategy for forming benzene rings.
- Aldol reaction,
- Diels-Alder reaction,
- Construction of benzene ring,
- Synthesis
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