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Oxidation of Amines to Nitroso Compounds

Oxidation of Amines to N-Nitrosamines: Introduction

Starting materials

  • Primary or secondary amines
  • Nitrous acid (HNO2 or NaNO2/HCl) or nitrosyl cation (NO+ )

Reaction principle

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.

Secondary amine
Primary amine


N-Acyl-N-nitrosamines are used for the preparation of diazoalkanes.

Biological importance

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.

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