Nitro-diphenyl-acetonitrile

Activated nitro and halo substituents have been efficiently replaced by a variety of alkyl groups via SsAx reaction with carbanions. Examples include the displacement of the nitro group in compounds (10 X = 4-PhCO, 4-MeOCO, 4-CN, 4-N02, 4-PhS02, 3,5-(CF3>2) by the anion of 2-nitropropane in HMPA at room temperature (equation 2),83 and the reaction of p-dinitrobenzene with several ketones, esters and nitriles (RH equation 3) in Bu OK/liquid NH3 at -70 C.84 Interestingly, under the latter reaction conditions, p-chloronitrobenzene gave the product of alkylation rather than of SNAr displacement of chloride, as in equation (4).85 Further examples include the dehalogenation of p-halonitrobenzenes by 9-fluorenyl anions in DMSO at room temperature,34 and dehalogenation and denitration reactions by the carbanions of phenyl- and diphenyl-acetonitrile in DMSO or under PTC conditions.86... 

Acetic acid, nitro-, methyl ester, 55, 77, 78 Acetic acid, trifluoro-, 55 70 Acetonitrile, diphenyl-, 55, 94, 102 Acetonitrile, diphenyl-2-(l-ethoxyethenyl)-[ Acetonitrile, diphenyl-2-(l-ethoxy-vinyl)-, 55, 102... 

Diphenyl-4-nitro-l-oxo-butan wird auf diese Weise aus 1,3-Diphenyl-3-oxo-propen in Gegenwart von Kaliumfluorid/Diazomethan in Toluol oder Acetonitril (3-4 d) zu 50 100% erhalten3. 

Die Fluorid-Ionen-katalysierte Michael-Addition von l,l-Diphenyl-2-nitro-ethcn mit Acetonitril liefert 3,3-Diphenyl-4-nilro-butansdure-nitril (45%)l,s 2 ... 

Methylation of 3-nitro-2,5-diphenyl-1,4-dithiin using a mixture of methyl iodide and silver tetrafluoroborate in methylene chloride/acetonitrile/nitromethane gave a mixture of two products in the ratio of 3 1. The major product was shown to be l-methyl-6-nitro-2,5-diphenyl-l,4-dithiinium tetrafluoroborate and the minor component to be 3-(dimethylsulphonio)-5-nitro-2,4-diphenylthiophene tetrafluoroborate. 

There has been much interest in the reactivity of nitronium salts, for example, toward amides in acetonitrile,the oxidation of alkanes in acetonitrile (via a carbenium ion intermediate),and toward organic sulfides, phosphines, arsines, and stibines. Reaction with diaryl, aryl alkyl, and dialkyl sulfides give sulfoxides, but a few percent of the ring C-nitro products were found for diphenyl sulfide. This is a result of the equilibrium between nitrito onium ions ] X-ONO and nitronium ions This is the first demonstration of the ambident reactivity... 

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