Tetrabutylammonium perruthenate

Catalytic oxidant.1 In combination with N-methylmorpholine N-oxide (7,244) as the stoichiometric oxidant, this ruthenium compound can be used as a catalytic oxidant for oxidation of alcohols to aldehydes or ketones in high yield in CH2C12 at 25°. Addition of 4A molecular sieves is generally beneficial. Racemization is not a problem in oxidation of alcohols with an adjacent chiral center. Tetrabutylammonium perruthenate can also be used as a catalytic oxidant, but the preparation is less convenient. 

Dengel, A. C., Hudson, R. A., Griffith, W. P. Tetrabutylammonium perruthenate a new mild oxidant for alcohols. Transition Metal Chemistry (Dordrecht, Netherlands) 1985, 10, 98-99. 

Griffith, W. P., Ley, S. V., Whitcombe, G. P., White, A. D. Preparation and use of tetrabutylammonium perruthenate (TBAP reagent) and tetrapropylammonium perruthenate (TPAP reagent) as new catalytic oxidants for alcohols. J. Chem. Soc., Chem. Common. 1987,1625-1627. 

A, A, A, A -tetramethylethylenediamine trimethyl orthoformate tetrapropylammonium perruthenate tetraphenylporphyrin sulfonated triphenylphosphine triisopropylbenzensulfonyl chloride triphenylcarbenium tetrafluoroborate tetrabutylammonium triphenylmethanethiolate toluenesulfonyl... 

Polymer supported sodium ruthenate is able to catalyze the oxidation of alcohols with iodosobenzene or tetrabutylammonium periodate in CH2CI2.8 It is not clear whether the primary oxidant is ruthenate or perruthenate. 

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... 

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