Dinitrogen Tetroxide–Impregnated Charcoal (N₂O₄/Charcoal): Selective Nitrosation of Amines, Amides, Ureas, and Thiols

Abstract

Efficient N‐nitrosation of amines, amides, and ureas, and also S‐nitrosation of thiols were performed with dinitrogen tetroxide impregnated on activated charcoal (N₂O₄/charcoal) in CH₂Cl₂ at room temperature. High selectivity was observed for N‐nitrosation of dialkyl amines, N‐alkylamides and N‐alkylureas. Dealkylation and N‐nitrosation of trialkylamines were also performed by this reagent.

Keywords:

• Dinitrogen tetroxide
• nitrosamines
• nitrosamides
• nitrosothiols

Acknowledgments

The authors are thankful to Shiraz University Research Council for the partial support of this work.