Cyclopropenium-Activated DMSO for Swern-Type Oxidation

Tianfo Guo, Yu Gao, Zhenjiang Li*, Jingjing Liu, Kai Guo*

*College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Road South, Nanjing 211816, P. R. of China, Email: guoknjtech.edu.cn, zjlinjtech.edu.cn

T. Guo, Y. Gao, Z. Li, J. Liu, K. Guo, Synlett, 2019, 30, 329-332.

DOI: 10.1055/s-0037-1611183

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Abstract

Swern oxidation using the volatile oxalyl chloride as an activator requires reaction temperatures below -60 °C. 3,3-Dichloro-1,2-diphenylcyclopropene (DDC) can be used as a new activator at −20 °C. This convenient new protocol offers mild and fast reactions. Furthermore, the activator DDC is easy to handle, and diphenylcyclopropenone can be recovered quantitively.

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Key Words

alcohols, aldehydes, ketones, cyclopropenium ion, Swern oxidation, DMSO

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ID: J72-Y2019