Organic Chemistry Portal



Dichloroimidazolidinedione-Activated Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams

Yu Gao, Jingjing Liu, Zhenjiang Li, Tianfo Guo, Songquan Xu, Hui Zhu, Fulan Wei, Siming Chen, Hailemariam Gebru and Kai Guo*

*State Key Laboratory of Materials-Oriented Chemical Engineering, College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Road South, Nanjing 211816, China, Email:

Y. Gao, J. Liu, Z. Li, T. Guo, S. Xu, H. Zhu, F. Wei, S. Chen, H. Gebru, K. Guo, J. Org. Chem., 2018, 83, 2040-2049.

DOI: 10.1021/acs.joc.7b02983


Substoichiometric amounts of the readily available and economical geminal dichloroimidazolidinediones (DCIDs) enable an activation of the Beckmann rearrangement via a unique self-propagating mechanism. 23 rearrangements have been performed with excellent yields in a short time, including a substrate for synthesizing the monomer of nylon-12 and a complicated steroidal substrate on a preparative scale.

see article for more examples

Key Words

Beckmann Rearrangement

ID: J42-Y2018