β-Substituierte Enamine, 12. Mitt. N-Aryl-2-nitro- und N-Aryl-2-chlor-2-nitro-enamine

β-Substituted Enamines, XII. N-Aryl-2-nitro- and N-Aryl-2-chloro-2-nitroenamines 1-Chloro-1-nitroacetone ( 4 ), obtained from sulfuryl chloride and nitroacetone ( 2 ), is a stable compound. In the presence of alkali it forms 1-chloro-1-isonitrosoacetone ( 9 ). With diazomethane it reacts to give 1 -chloro-1-methoxyiminoacetone ( 8 ). By aniline 4 is cleaved with the formation of acetanilide and chloronitromethane. In the presence of titanium tetrachloride, however, condensation to 1-chloro-1-nitro-2-phenylaminopropene ( 3a ) is achieved. The condensation of nitroacetone ( 2 ) with primary aromatic amines via β-nitroenamines 1 and subsequent chlorination with N-chlorosuccinimide also leads to N-aryl-2-chloro-2-nitroenamines 3 .