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organic compounds containing a nitroso group, —N═O, bound directly to a carbon atom—for example, nitroso-tert-butane, (CH3)3C—N═O; nitrosoben-zene, C6H5—N═O; trifluoronitrosomethane, CF3N═O; and p-nitrosodimethylaniline, (CH3)2N—C6H4—N═O. Many nitroso compounds exist in a dimeric form that converts readily upon melting, dissolution, or distillation into the monomeric form: (R3CNO)2 ⇄ 2R3CNO. Monomeric nitroso compounds are colored (blue or greenish) liquids or gases; the dimers are colorless solids.
Nitroso compounds are very reactive; they may be oxidized to the corresponding nitro compounds, reduced to amines (or hydroxylamines), and relatively easily condensed with amines (in a manner similar to aldehydes and ketones). Nitroso compounds are produced from olefins, amines, nitro compounds, and oximes by various methods. Aromatic nitroso compounds are used as dyes, intermediates in organic synthesis, and analytical reagents; fluorine-containing nitroso compounds (for example, CF3NO) are used in the production of heat-resistant rubbers.
Nitroso compounds are sometimes considered to include all compounds containing a nitroso group—for example, nitrosoamines, R2N—NO.