Ammonium nitrate-Trifluoroacetic

Tetrachlorooxanthrene has been dinitrated with either nitric acid/acetic anhydride or with ammonium nitrate/trifluoroacetic anhydride to give the 2,7-dinitro compound, and dinitration of the... 

Acetamido-3,4-di-61-acetyl-6-deoxy-D-glucal on reaction with ammonium nitrate-trifluoroacetic anhydride in aqueous sodium bicarbonate affords the unsaturated pentose compound 31 whereas reaction with mercury(II) sulfate and sulfuric acid gave the expected -alkene 32. ... 

Several electrophiles, such as acetic anhydride, nitric acid or alternative nitrating agents, such as ammonium nitrate in trifluoroacetic anhydride (41), or sodium hypochlorite, react at N-1, which is followed by reaction at N-3 under suitable conditions. In the case of acetic anhydride, the reaction can take place exclusively at N-3 if N-1 is hindered this fact has served as a criterion for studying the stereochemistry of 5-spirohydantoin derivatives (42,43). 

Amide nitrogens can be protected by 4-methoxy or 2,4-dimethoxyphenyl groups. The protecting group can be removed by oxidation with ceric ammonium nitrate.243 2,4-Dimethoxybenzyl groups can be removed using anhydrous trifluoroacetic acid.244... 

Nitration of the potassium enolates of cycloalkanones with pentyl nitrate81 or nitration of silyl enol ethers with nitronium tetrafluoroborate82 provides a method for the preparation of cyclic a-nitro ketones. Trifluoroacetyl nitrate generated from trifluoroacetic anhydride and ammonium nitrate is a mild and effective nitrating reagent for enol acetates (Eq. 2.41).83... 

Several additives were tested with a series of explosives in order to enhance ESI intensities [15—17]. Nitramine and nitrate ester explosives showed enhanced response for ammonium nitrate additive, by forming [M + NOs] adduct ions in the negative-ion mode. Nitrate adduct ions were more intense than trifluoroacetate (TFA) or chloride adduct ions by a factor of 6-40. The base peak in the negative-ion mass spectrum of TNT, with 1 mM ammonium nitrate in the mobile phase was at m/z 226 due to the [M-H] ion. 

A mixture of silver nitrite and iodine reacts with alkenes to give jS-nitroalkyl iodides, and therefore, provides a convenient route to a-nitroalkenes. Treatment of alkenes with ammonium nitrate and trifluoroacetic anhydride in the presence of ammonium bromide, followed by... 

Toluene, Sulfuric acid. Nitric acid Nitric acid. Sulfuric acid. Toluene Toluene, Sulfuric acid. Nitric acid. Methylene chloride Toluene, Sulfuric acid. Potassium nitrate. Methylene chloride Toluene, Sulfuric acid. Sodium nitrate. Methylene chloride Toluene, Sulfuric acid. Nitric acid. Premium unleaded gasoline Trifluoroacetic anhydride, Nitromethane, Ammonium nitrate, NIHT HCL, Ethyl acetate... 

TNTC Trifluoroacetic anhydride, Nitromethane, Ammonium nitrate, NIHT HCL, Ethyl acetate Secondary high explosive ... 

Among other oxidizing agents286 that have been used to accomplish the conversion of ArCHj to ArCHO are ceric ammonium nitrate,287 ceric trifluoroacetate,288 benzeneseleninic anhydride,257 KMnCV-EtjN,289 and silver(II) oxide.290 Oxidation of ArCHj to carboxylic acids is considered at 9 11. 

Cerium(IV) ammonium nitrate, 67 Thallium(III) trifluoroacetate, 295 Allylic iodides... 

Yamashiro et al. 1972), boron trifluoride etherate in acetic acid (Schnabel et al. 1971), trimethylsylil triflate (Schmidt et al. 1987), trimethylsilyl perchlorate (Vorbrueggen Krolikiewicz 1975), and, most frequently, trifluoroacetic acid (Farowicki Kocienski 1995 and references therein). Deprotection of the /-HOC group under neutral conditions was not described until recently, yet it is highly desirable. Now it has been found that the tert-butoxycarbonyl protecting group for amines, alcohols, or thiols is removed efficiently (90-99% yield) with use of 0.2 equivalent of cerium ammonium nitrate in acetonitrile at 80°C (Hwu et al. 1996) ... 

W. W. Zajac, P. Dampawan, and D. Ditrow, Reaction of glycals with trifluoroacetic anhydride and ammonium nitrate a novel cleavage reaction of glycals, J. Org. Chem., 51 (1986) 2617-2618. 

The N-desilylation of 1-trimethylsilyl- or 1 -(// rt-butyldimethylsilyl)-2-azctidinones is a commonly used process in 2-azetidinone chemistry. The leri-b11toxycarbonyI group is readily removed with trifluoroacetic acid, while the 4-methox-yphenyl protecting group is conveniently removed by ceric ammonium nitrate, or anodic oxidation (Scheme 87). 

Ac, acetyl AIBN, azobis(isobutanonitrile) All, allyl AR, aryl Bn, benzyl f-BOC, ferf-butoxycarbonyl Bu, Butyl Bz, benzoyl CAN, ceric ammonium nitrate Cbz, benzyloxycarbonyl m-CPBA, m-chloroperoxybenzoic acid DAST, diethylaminosulfur trifluoride DBU, l,8-diazabicyclo[5.4.0]undec-7-ene DCC, /V. /V - d i eye I oh e x y I c ar bo -diimide DCM, dichloromethyl DCMME, dichloromethyl methyl ether DDQ, 2,3-dichloro-5,6-dicyano-l,4-benzoquinone DEAD, diethyl azodicarboxylate l-(+)-DET, L-(+)-diethyl tartrate l-DIPT, L-diisopropyl tartrate d-DIPT, D-diisopropyl tartrate DMAP, 4-dimethylaminopyridine DME, 1,2-dimethoxyethane DMF, /V./V-dimethylformamide DMP, 2,2-dimethoxypropane Et, ethyl Im, imidazole KHMDS, potassium hexamethyldisilazane Me, methyl Me2SO, dimethyl sulfoxide MOM, methoxymethyl MOMC1, methoxymethyl chloride Ms, methylsulfonyl MS, molecular sieves NBS, N-bromosuccinimide NIS, /V-iodosuccinimide NMO, /V-methylmorpho-line N-oxide PCC, pyridinium chlorochromate Ph, phenyl PMB, / -methoxvbenzyl PPTs, pyridiniump-toluenesulfonate i-Pr, isopropyl Py, pyridine rt, room temperature TBAF, tetrabutylammonium fluoride TBS, ferf-butyl dimethylsilyl TBDMSC1, f-butylchlorodimethylsilane Tf, trifhioromethylsulfonyl Tf20, trifluoromethylsulfonic anhydride TFA, trifluoroacetic acid THF, tetrahydrofuran TMS, trimethylsilyl TPAP, tetra-n-propylammonium perruthenate / -TsOH. / -toluenesulfonic acid... 

Summary TNTC is prepared by treating NIHT.HC1 with nitromethane and ammonium nitrate in the presence of trifluoroacetic anhydride. After the reaction, the TNTC is contaminated with a by-product and hence needs to be purified. To do this, the contaminated TNTC is treated with ethyl acetate, and reciystallized. Commercial Industrial note For related, or similar information, see Application No. 471,906, January 29, 1990, by Gencorp Aerojet, to Der-Shing Hunag, Folsom, CA. Part or parts of this laboratory process may be protected by international, and/or commercial/industrial processes. Before using this process to legally manufacture the mentioned explosive, with intent to sell, consult any protected commercial or industrial processes related to, similar to, or additional to, the process discussed in this procedure. This process may be used to legally prepare the mentioned explosive for laboratory, educational, or research purposes. 

Trifluoroacetyl nitrate, CF3COONO2 (1). The reagent is prepared in situ from ammonium nitrate (NH4NO3) and trifluoroacetic anhydride. 

Direct N-nitration of secondary amines by nitric acid is possible only for weakly basic amines. The more basic amines can be nitrated under neutral conditions widi reagents such as dinitrogen pentoxide and nitronium tetrafluoroborate, but nitrosamines are significant by-products. The nitrate ester CF3CMe20N02 has been recommended as a nonacidic nitrating agent for secondary amines which avoids the problem of contamination of the products by A(-nitrosamines piperidine and pyrrolidine were nitrated in yields of 75% and 72%, respectively. Amides and imides are efficiendy N-nitrated using ammonium nitrate in trifluoroacetic anhydride. ... 

Most aromatic compounds, whether of high or low reactivity, can be nitrated, because a wide variety of nitrating agents is available. For benzene, the simple alkylbenzenes, and less reactive compounds, the most common reagent is a mixture of concentrated nitric and sulfuric acids,but for active substrates, the reaction can be carried out with nitric acid alone, or in water, acetic acid, acetic anhydride, or chloroform.Nitric acid in acetic anhydride/trifluoroacetic anhydride on zeolite H-(3 was used to convert toluene to 2,4-dinitrotoluene, and AcONOi on clay converted ethylbenzene to ortho-para nitro ethylbenzene. " In fact, these milder conditions are necessary for active compounds, such as amines, phenols, and pyrroles, since reaction with mixed nitric and sulfuric acids would oxidize these substrates. With active substrates, such as amines and phenols, nitration can be accomplished by nitrosation under oxidizing conditions with a mixture of dilute nitrous and nitric acids.A mixture of N02/02/Fe(acac)3 can be used for active compounds, as can NaN02 with trichloroisocyanuric acid on wet silica gel, or N2O4 and silica acetate. Trimethoxybenzenes were nitrated easily with ceric ammonium nitrate on silica gel, and mesitylene was nitrated in an... 

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