Organic Chemistry Portal



Diversity-Oriented Synthesis of N,N,O-Trisubstituted Hydroxylamines from Alcohols and Amines by N-O Bond Formation

Jarvis Hill, Asiri A. Hettikankanamalage and David Crich*

*Department of Pharmaceutical and Biomedical Sciences, and Department of Chemistry, University of Georgia, 140 Cedar Street, Athens, Georgia 30602, United States, Email:

J. Hill, A. A. Hettikankanamalage, D. Crich, J. Am. Chem. Soc., 2020, 142, 14286-14294.

DOI: 10.1021/jacs.0c05991


Magnesium dialkylamides react with alcohol-derived 2-methyl-2-tetrahydropyranyl alkyl peroxides (MTHPs) in tetrahydrofuran at 0C to give N,N,O-trisubstituted hydroxylamines in very good yields. A wide range of substrates are compatible with the described reaction.

see article for more examples

proposed mechanism

Key Words


ID: J48-Y2020