Nitryl chloride, addition

Nitryl chloride (NO2CI) also adds to alkenes, to give p-halo nitro compounds, but this is a free-radical process. The NO2 goes to the less-substituted carbon. Nitryl chloride also adds to triple bonds to give the expected l-nitro-2-chloro alkenes. The compound FNO2 can be added to alkenes by treatment with HF in HNOa or by addition of the alkene to a solution of nitronium tetrafluoroborate (NOJBF4, see 11-2) in 70% polyhydrogen fluoride-pyridine solution (see also 15-37). [Pg.1046]

Nitryl halides have been more popular reagents. Treatment of substituted styrenes with iodine and sodium nitrite leads to Markovnikov addition of NO2I (electropositive NO2) to the double bond. Elimination of HI affords (3-nitrostyrenes149150 as shown in Scheme 73.149 ( )-2-nitro-l-(trimethylsilyl)ethylene has been prepared by addition of nitryl chloride to trimethylsilylethylene, followed by elimination of HI. The author advertises the use of NO2CI and the other reagents involved as more economical than some of the other approaches to the nitroalkene (Scheme 74).151... [Pg.357]

The existence of similar addition products must be mentioned here. Steinkopf and Kiihnel [23] observed that benzene reacted with nitryl chloride at room temperature under pressure to yield l-chloro-2-nitrocyclohexadiene, which on heating released a molecule of hydrogen chloride giving nitrobenzene ... [Pg.58]

Olefin additions Bromine azide. Bromine chloride. Bromine (chlorine) dipyridine nitrate. N-Bromoacetamine. N-Bromoacetamide-DMSO-Water. N-Bromoacetamide-Hydrogen fluoride. n-Butyllithium. Dichloroketene. Dichloromethyl 2-chloromethyl ether. N,N-Dichlorourethane. Dichlorovinylene carbonate. Difluoramine. Ethyl azidoformate. Ethyl bromoacetate. Iodine azide. Iodine isocyanate. Iodine nitrate, lodobenzene dichloride. 1-lodoheptafluoropropane. Mercuric acetate. Nitrosyl chloride. Nitrosyl fluoride. Nitryl iodide. Rhodium trichloride. Silver fluoride. [Pg.242]

OLEFIN ADDITIONS Benzenesulfonyl azide. Chlorosulfonyl isocyanate. Chiom-ous chloride. Cyanamlde. Dichloroketene. Dinitrogen tetroxide-Iodine. Diphenyl-ketene. Ethoxyketene. Fluoroxytrifluoro-methane. Iodine. Iodine azide. Iodine isocyanate. Iodobenzene dichloride. Mercuric azide. Nitrosyl chloride. Nitrosyl fluoride. Nitryl iodide. Potassium f-but-oxide-Bromoform (dibromocarbene). [Pg.179]