Nitrosation

Nitrosation is a process of converting organic compounds into nitroso derivatives, i.e. compounds containing the R-NO functionality.

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C-Nitroso compounds

C-Nitroso compounds, such as nitrosobenzene, are typically prepared by oxidation of hydroxylamines:

RNHOH + [O] → RNO + H₂O

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N-nitrosamines

N-nitrosamines, including the carcinogenic variety, arise from the reaction of nitrite sources with amino compounds. Typically this reaction proceeds via the attack of the nitrosonium electrophile on an amine:

NO₂^- + 2 H⁺ → NO⁺ + H₂O

R₂NH + NO+ → R₂N-NO + H⁺

Reaction Mechanism

Formation of an N-nitrosamine