University Chemistry ›› 2022, Vol. 37 ›› Issue (5): 2110099.doi: 10.3866/PKU.DXHX202110099

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Selective Epoxidation of Carvone

Ling Li, Xueyan Zhang, Xiaoman Wang, Jian Ling, Yong Shi()   

  • Received:2021-10-29 Accepted:2021-11-04 Published:2022-03-22
  • Contact: Yong Shi


Selectivity is a core organic chemistry concept and is often a key issue in organic chemistry research. In this experiment, (R)-(−)-carvone was used as a substrate upon which two oxidation methods were employed to selectively give two different products. The epoxidation of the two double bonds of carvone shows chemoselectivity, while whether the corresponding product is a mixture of isomers shows stereoselectivity. Since this experiment features inexpensive reagents, simple operation and workup procedures, and high yields, it is suitable for organic chemistry experimental teaching, deepening undergraduates' understanding of chemoselectivity and stereoselectivity.

Key words: Selectivity, Carvone, Epoxidation, Chemoselectivity, Stereoselectivity