Nitroso

  Nitroso refers to a functional group in organic chemistry which has the general formula RNO. Nitroso compounds can be prepared by the reduction of nitro compounds or by the oxidation of hydroxylamines. A good example is (CH₃)₃CNO, known formally as 2-methyl-2-nitrosopropane, or t-BuNO, which is prepared by the following sequence:^[1]

(CH₃)₃CNH₂ → (CH₃)₃CNO₂

(CH₃)₃CNO₂ → (CH₃)₃CNHOH

(CH₃)₃CNHOH → (CH₃)₃CNO

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(CH₃)₃CNO is blue and exists in solution in equilibrium with its dimer, which is colorless, m.p. 80 − 81 °C.

In the Fischer-Hepp rearrangement aromatic 4-nitroso-anilines are prepared from the corresponding nitrosamines. Another named reaction involving a nitroso compound is the Barton reaction.

See also

• Nitrosamine, the functional group with the NO attached to an amine, such as R₂N-NO
• Nitrosobenzene

References

1. ^ A. Calder, A. R. Forrester, and S. P. Hepburn 2-Methyl-2-nitrosopropane and Its Dimer Organic Syntheses, Coll. Vol. 6, p.803; Vol. 52, p.77. Link