Organic Chemistry Portal



Reductive Cleavage of Unactivated Carbon-Cyano Bonds under Ammonia-Free Birch Conditions

Yuxuan Ding, Shihui Luo, Lifu Ma* and Jie An*

*Tianjin University, Tianjin 300072; China Agricultural University, No. 2, Yuanmingyuan West Road, Beijing 100193, China, Email:,

Y. Ding, S. Luo, L. Ma, J. An, J. Org. Chem., 2019, 84, 15827-15833.

DOI: 10.1021/acs.joc.9b02028

see article for more reactions


Single-electron-transfer conditions using Na/15-crown-5/H2O enable a reductive cleavage of unactivated carbon-cyano bonds in aliphatic nitriles. Compared with the Na/NH3 electride system generated under traditional Birch conditions, this ammonia-free electride system is more practical and features better reactivity and chemoselectivity.

see article for more examples

Reductive Deuteration of Nitriles: The Synthesis of α,α-Dideuterio Amines by Sodium-Mediated Electron Transfer Reactions

Y. Ding, S. Luo, A. Adijiang, H. Zhao, J. An, J. Org. Chem., 2018, 83, 12269-12274.

Key Words

decyanation, sodium

ID: J42-Y2019