Tetrabutylammonium chlorochromate

Tetrabutylammonium chlorochromate [54712-57-1 ] M 377.9, m 184-185 . Recrystd EtOAc-hexane. IR v 920cm in CHCI3 [Synthesis 749 1983]. Powerful oxidant. 

Tetrabutylammonium chlorochromate, (C4H9)4XCr03CI, is formed by adding a solution of chromium trioxide in concentrated hydrochloric acid to a solution of tetrabutylammonium hydrogen sulfate in 5 N hydrochloric acid at 0 °C. The dry compound is used in chloroform for the oxidation of alcohols to carbonyl compounds and the oxidative coupling of thiols to disulfides [619],... 

Instead of pyridine, 4-dimethylaminopyridine can be converted into a chlorochromate, and the complex can be used to oxidize benzylic alcohols to aldehydes [530]. Also, tetrabutylammonium chlorochromate gives good yields of unsaturated and aromatic aldehydes from the respective alcohols [619]. 

Chemicals AIBN CAN DIBAL DMAP DMSO HMPA LAH LDA mCPBA NBS NCS or PCC PDC Py TBAF TEMPO a.a -azobislisobutyronitrile) cerium(IV) ammonium nitrate diisobutylaluminium hydride 4-(dimethylamino)pyridine dimethyl sulfoxide hexamethylphosphoramide lithium aluminum hydride lithium diisopropylamide m-chloroperoxybenzoic acid A-bromosuccinimide A-chlorosuccinimide superoxide anion radical pyridinium chlorochromate pyridinium dichromate pyridine tetrabutylammonium fluoride 2,2,6,6-tetramethyl-l-piperidinyloxy free radical... 

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... 

Desilylation with tetrabutylammonium fluoride gave a mixture of hydroxy acetates, which were oxidised with pyridinium chlorochromate to the ketoacetates 94. (5-Elimination under basic conditions and deacetylation gave the mixture of diols 95 and 8-epi-95, which were separated by chromatography. 

Borabicyclo[3.3. l]nonane Butylated hydroxytoluene 3,4-Dihydro-2//-pyran Diisobutylaluminum hydride V,jV-Dimethylformamide Dimethyl sulfoxide Hexamethylphosphoric triamide Lithium aluminum hydride Lithium diisopropylamide Minimum inhibitory concentration Pyridinium chlorochromate Pyridinium dichromate S-adenosylmethionine Tetrabutylammonium fluoride tert-Butyldimethylsilyl tert-Butyldimethylsilyl chloride Tetrahydrofuran Trimethylsilyl cyanide... 

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