Nitroso Compounds by Reaction of Organomercurials with Nitrosyl Chloride

By the reaction of RHgX (X = Cl, Br, OAc) with NOC1, mercury is eliminated as CIHgX and, if R is aromatic, nitroso compounds are obtained, i.e., nitrosobenzene, 1-nitrosonaphthalene, 4-nitroso-lV^V- dimethylaniline, 2-nitrosophenol, 4-nitrosophenol and methyl 3-ni- trososalicylate. If R is aliphatic or alicyclic, with RHgX to NOC1 1 : 3, gem-chloronitroso compounds are obtained that have not been described previously, i.e., 2-chloro-2-nitrosocyclohexanol, l-acetoxy-2- chloro-2-nitrosocyclohexane, l-chloro-2-methoxy-l-nitrosocyclopentane, methyl 2-chloro-2-nitroso-3-methoxypropionate, 1-chloro-l-nitroso- ethane and 2-chloro-2-nitrosoethanol. All products have been characterized by chemical and IR spectral analysis