Oxidation of Amines to Nitroso Compounds
Oxidation of Amines to N-Nitrosamines: Introduction
- Primary or secondary amines
- Nitrous acid (HNO2 or NaNO2/HCl) or nitrosyl cation (NO+ )
Substitution of a hydrogen atom of primary or secondary amines by a nitroso group.
Primary amines, because of their high reactivity, immediately react to form diazo derivatives.
N-Acyl-N-nitrosamines are used for the preparation of diazoalkanes.
With the exception of secondary nitrosoamines without α-hydrogen, nitrosamines are carcinogens. For example, they can be formed in the human stomach through intake of nitrite (meat curing salt) and subsequent reaction with amines which abound in the human body.