1- Phenyl-2-nitroethane

Konovalov [15] nitrated aliphatic hydrocarbons in sealed tubes at 120-130°C, using dilute nitric acid of concentration 6.5-19%. From normal hydrocarbons he obtained secondary nitro compounds in yields varying from 40% (2-nitro-hexane from hexane) to 49-50% (2-nitrooctane from octane). Aromatic hydrocarbons with an aliphatic substituted group when nitrated under the same conditions gave nitro derivatives with a nitro group in the side chain. For example, ethylbenzene, when nitrated with 12.5% nitric acid at 105-108°C, gives phenyl-nitroethane in 44% yield. The optimum yield is obtained with 13% acid. 

Indolizine, hydroxy-conformations, 4, 451 GLC retention times, 4, 451 synthesis, 4, 121 tautomerism, 4, 198, 452 Indolizine, 2-hydroxy-synthesis, 4, 463 Indolizine, 8-hydroxy-conformation, 4, 452 Indolizine, 2-hydroxymethyl-synthesis, 4, 461 Indolizine, 3-hydroxymethyl-synthesis, 4, 461 Indolizine, 6-hydroxymethyl-synthesis, 4, 461 Indolizine, methyl-mass spectra, 4, 187, 450 NM 4, 448 Indolizine, 2-methyl-diazo coupling, 4, 454 mass spectra, 2, 529, 4, 450 nitration, 4, 50, 454 nitrosation, 4, 454 reaction with diaryl disulfide, 4, 460 reaction with nitroethane, 4, 460 Indolizine, 3-methyl-basicity, 4, 454 Indolizine, 5-methyl-acidity, 4, 461 synthesis, 4, 466 Indolizine, 6-methyl-mass spectra, 4, 450 Indolizine, l-methyl-2-phenyl-nitration, 4, 454 nitrosation, 4, 454, 455 Indolizine, 3-methyl-2-phenyl-reaction... 

Nitrostyrene requires from 60-90 hours for the uptake of 1 mole of hydrogen. The product, l-phenyl-2-nitroethane, is purified by distillation, bp 76-7770.5 mm. 

A mixture of 1.1 g of 2-amino-1-(4-methylmercaptophenyl)-1,3-propanediol, obtained as described above and 1.6 ml of ethyl dichloroacetate was heated on a steam bath for three hours. The resulting viscous yellow oil was dissolved in 25 ml of ethylene chloride and filtered hot with charcoal, and the filtrate was allowed to cool to about 25°C. From the filtrate there separated 0,92 g of tiny white leaflets which were collected on a filter. Recrystallization of this product, which was a dextro-rotary form of 2-dichloroacetylamino-1-(4-methylmercapto-phenyl)-1,3-propanediol from nitroethane yielded the pure product, which melted at 111.6°C to 112.6°C,... 

The anion of primary nitro compounds such as nitroethane reacts with hexamethylsilthiane 601 to give acetothiohydroxamic acid 1913 in 81% yield [117], whereas reaction with phenylthiotrimethylsilane 584 affords phenyl acetothiohy-droximate 1914 in 62% yield [117] (Scheme 32.33). Secondary nitro compounds... 

The Mukaiyama-Hoshino reaction between a nitroalkane and phenyl isocyanate generates a nitrile oxide, and this method has been used in the synthesis of 1,2,4-oxadiazoles as discussed in CHEC-II(1996) <1996CHEC-II(4)179>. In a more recent advance, nitroethane undergoes ultrasound-mediated cycloaddition with trichloroacetonitrile to give the extremely useful (see Equation 11) 5-trichloromethyl-l,2,4-oxadiazole 228 (Equation 45) <1995TL4471>. 

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

Substituted-l-Phenyl-2-Nitropropenes. JOC, 18, 1 (1953). 5 g of 2,5-Dimethoxy-4-bromobenzaldehyde, 5 ml of nitroethane (EtN02), and 2 g of ammonium acetate are added to 20 ml of glacial acetic acid. The resulting solution is refluxed for two hours and poured into ice water. If a solid product is obtained it is collected and recrystallized from methanol, ethanol, or acetic acid. If the product is an oil it is separated and crystallized from one of the above. 

The nitroethane cyclization of p-phenylglutaraldehyde (19) takes an analogous steric course. Only the major product, lf-methyl-l-nitro-4c-phenyl-cyclohexane-2c,6c-diol (20) was isolated in 50% yield >. The... 

With benzonitrile oxide (BNO) or acetonitrile oxide (ANO), obtained from benzhydroxamic chloride or from nitroethane and phenyl isocyanate in the presence of triethylamine, the l,2,4-oxadiazolo[2,3-h][l,3]oxazines 440 (87MRC635, 87T1931, 87T5461 91MRC706) were obtained. 

Ephedrine Ephedrine, L-erythro-l-phenyl-2-methylaminopropanol-l (11.3.4), is synthesized from benzaldehyde in a few different ways. According to the first, benzaldehyde is condensed with nitroethane, giving 2-methyl-2-nitro-l-phenylethanol (11.3.2), which is reduced to 2-methyl-2-amino-l-phenylethanol (11.3.3). The necessary L-isomer is isolated from the mixture of isomers by crystallization. Methylation of this gives ephedrine (11.3.4) [52,53]. 

The anion of nitromethane (31) failed to react with Phi under irradiation in DMSO, as was the case with 1-AdI. However, when the reaction was carried out in the presence of acetone (27a) or pinacolone (27b) enolate ions, l-phenyl-2-nitroethane (161) was formed as major product, together with small amounts of benzene and toluene (equation 104). No products from the coupling with the ketone enolate ions were found169... 

Additions of the Michael type of nucleophiles to the carbon-carbon double bond of thiete 1,1-dioxides to give 3-substituted thietane 1,1-dioxides occur readily. The addition of hydrogen has been discussed in Section A. Nucleophiles include cyanide, the anion of nitroethane, the lithium salt of r-butyl o-tolyl sulfone, dimethylamine, cyclohexylamine, ethoxide, and hydrogen sulfide. The reaction is exemplified by the synthesis of 278. Additions to 3-chloro-2H-thiete 1,1-dioxide most likely proceed by an addition-elimination mechanism an example is shown for the addition of the anion of dimethylmalonate to give 279. The replacement of a 3-morpholinyl group by a 3-A methyl-A-phenylamino group in thiete 1,1-dioxide is another example of addition-elimination. An addition of ethoxide with elimination of p-nitrophenyl anion may occur with 268 (Ar = / -N02C6H4). " Addition of bromine via N-bromo-succinimide to the double bond of 4-phenyl-2H-thiete 1,1-dioxide occurs only in 1.5% yield. ... 

According to a patent,126 2-nitro-l-phenyl-1-propanol is obtained by adding a solution of nitroethane gradually, with stirring, to the benzaldehyde bisulfite compound at room temperature. 

---