Acetyl fluoride oxidation

Before describing the preparation and properties of trifluoroacetate compounds in general, particular consideration will be given to the parent acid. The normal commercial preparation of trifluoroacetic acid is the electrolytic fluorination of acetyl fluoride or chloride 210). Other preparative methods include the oxidation of trifluorotoluidine or other trifluoromethyl aryl derivatives 247) and the hydrolysis of trifluoro-acetylchloride (6). 

Purine, 6-bromo-9-/3-D-(2,3,5-tri-0-acetyl)ribofuranosyl-synthesis, 5, 598 Purine, 6-carboxy-reactions, 5, 549 Purine, 8-carboxy-reactions, 5, 549 Purine, 2-chloro-reactions, 5, 561 synthesis, 5, 597 Purine, 6-chloro-alkylation, 5, 529 glycosylation, 5, 529 oxidation, 5, 539 3-oxides reactions, 5, 554 synthesis, 5, 595 reactions, 5, 561, 595 with ammonia, 5, 562 with fluorides, 5, 563 with trimethylamine, 5, 562 9- -D-ribofuranoside synthesis, 5, 560 synthesis, 5, 597, 598 Purine, 8-chloro-amination, 5, 542 Purine, 6-chloro-8-ethoxy-synthesis, 5, 591 Purine, 6-chloro-9-ethyl-dipole moment, 5, 522 Purine, 6-chloro-2-fluoro-riboside... 

Dehydrochlorination of bis(tnfluoromethylthio)acetyl chloride with calcium oxide gives bis(trifluoromethylthio)ketene [5] (equation 6) Elimination of hydrogen chloride or hydrogen bromide by means of tetrabutylammonium or potassium fluoride from vinylic chlorides or bromides leads to acetylenes or allenes [6 (equation 7) Addition of dicyclohexyl-18-crown-6 ether raises the yields of potassium fluoride-promoted elimination of hydrogen bromide from (Z)-P-bromo-p-ni-trostyrene in acetonitrile from 0 to 53-71 % In dimethyl formamide, yields increase from 28-35% to 58-68%... 

Acetyl-3-methyl-4,5-dihydrothiophen-4-one Benzyl alcohol, Hydrogen bromide, Iron Benzyl bromide, Molecular sieve Benzyl chloride, Catalytic impurities Benzyl fluoride l,2-Bis(chloromethyl)benzene Ethylene oxide, Contaminants Furoyl chloride... 

Meyer H.Wehrli, Helv 20, 353(1937) CA 31, 5807(1937) 5)M.L.Wolfrom et al, JACS 65, 2084(1943) 6)M.L.Wolfrom et al, Ohio State Univ Final Rept, Project 459, Columbus, Ohio(Jan 1953)pp 1,3 34 Nitrated Deacetylated Chitine A wh flocculent ppt contg 11=6 to 11,9% nitrate N(as detd by DuPont nitrometer obtd by Wolfrom et al(Ref 3) by nitrating deacetylated chitin with 100% HNOj. The nitrated product represented the combined nitrate salt nitrate ester of deacetylated chitin. This substance contd one nitric acid salt unit per anhydro-o-glucosamine unit and 1.60-1.65 nitrate ester unit per anhydro-o-glucosamine anhydro -N-acetyl-D -glucosammine units. Attempts to nitrate deacetylated chitin by means of nitrogen pent oxide, in a non-aqueous medium y in the presence of sodium fluoride, by the method of Caesar(Ref 2) were unsuccessful mainly because of occlusion of NaF in the nitrated products(Ref 3)... 

The fluoride LXX is extremely stable toward alcohols, and sodium meth-oxide effects de-O-acetylation to give LXXI (a stable crystalline compound), leaving the fluoride group intact. 

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... 

Oxidation of Schiff bases of the monoamide 8 derived from diamino-maleonitrile gives 4-cyanoimidazole-5-carboxamides (Eq. 4). A new synthesis of 2-formyl-4-methyl-l-phenylimidazole 3-oxide (10) involves the fluoride-ion-promoted cyclization of the trimethylsilyl ether of JV-dichloro-acetyl-A-phenylaminopropanone oxime (9). ... 

In addition to the methods of preparation given in connection with the procedure for the acetylation of thiophene with acetyl chloride in the presence of stannic chloride, 2-acetothienone has been prepared from thiophene and either acetyl chloride or acetic anhydride in the presence of iodine, hydriodic acid, silica-metal oxides, zinc chloride, or inorganic oxyacids. It has also been prepared from thiophene and acetic acid in the presence of hydrogen fluoride or phosphorus pentoxide. The acylation in the presence of phosphorus pentoxide is particularly useful with higher aliphatic acids. ... 

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