This is essentially the same of more work for GBL, however some of the other uses might bee of interest.
Use of ruthenium tetroxide as a multi-purpose oxidant.
Berkowitz, Lewis M.; Rylander, Paul N.
J. Am. Chem. Soc. (1958), 80 6682-4.
Abstract: The scope of the oxidation reactions of RuO4 (I) was investigated. I was prepd. by the slow addn. of N NaBrO3 to 4.37 g. RuCl3 (contg. 18% H2O) in 80 ml. refluxing 0.5N HCl, while I and H2O distd. into an ice-cooled receiver. I (55% yield) was then decanted and dissolved in CCl4 to give a deep red soln. Alcs. were oxidized rapidly by I to carbonyl compds. Thus, I in CCl4 was added to 1.50 g. cyclohexanol in 10 ml. CCl4 at 10-15° (ice-cooling was required). After standing overnight at room temp. the mixt. gave 2.18 g. RuO2 and 93% (based on I) cyclohexanone. Similarly, the following compds. were prepd. from the corresponding alcs. in the indicated yields: l-menthone, 96%; 3-cholestanone, 49%; BzH, 90%. n-C6H13OH, however, gave only 10% n-C5H11CO2H even with excess alc. trans-1,2-Cyclohexanediol in H2O gave 15% dione (or oxo-alc.). Aldehydes were oxidized rapidly to acids to give 33% BzOH and 30% n-C6H13CO2H. Olefins were oxidized to aldehydes with C-C bond cleavage,(hmm...piperonal from piperine or from isosafrole? in contrast to OsO4 which gave diols. Thus, cyclohexene gave 10% adipaldehyde and 1-octene gave 12% n-C6H13CHO and (presumably) CH2O. The low yields were possibly due to the difficulty in sepg. the products from RuO2. Me cyclopropyl ketone reacted little, if at all, with I. A unique reaction of I was the oxidation of ethers to esters. Thus, 2.55 g. Bu2O and 1.91 g. I in CCl4 gave a quant. yield of PrCO2Bu,while tetrahydrofuran gave a nearly quant. yield of g-butyrolactone which could not be oxidized further. An attempted oxidation of ethylene oxide at 0° in CCl4 to an a-lactone (II) gave only a polymer, possibly derived from II. Tetrahydrofurfuryl alc. gave a compd., possibly an aldehyde lactone, forming a dinitrophenylhydrazone. Although esters were stable to I, amides were oxidized to imides. Thus, 1.33 g. g-butyrolactam and 1.69 g. I gave 49% succinimide. N-Heptanoyl-n-hexylamine similarly gave an imide. C6H6 and EtCHMePh gave immediate reactions with I to yield unidentified carbonyl compds. C5H5N, (PhCH2)2, Ph3CH, tetrahydronaphthalene, 1-O2NC10H7, (PhN:)2, PhC.tplbond.CH, and (PhC.tplbond.)2 also gave immediate reactions but no isolated products. Slower reactions of I with Am3N, Et2NH, and piperidine apparently gave amides, while n-C6H13NH2 apparently did not. Ru is less volatile, less toxic, less expensive, and more readily available than Os.
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