5729-92-0Relevant articles and documents
Diastereo and enantioselective synthesis of 1,2-diols promoted by electrophilic selenium reagents
Santi,Tiecco,Testaferri,Tomassini,Santoro,Bizzoca
experimental part, p. 956 - 960 (2009/04/06)
Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO3H generated "in situ" by oxidation of (PhSe)2 with (NH4)2S2O8 at reflux in a 3:1 mixture of MeCN-H2O. I
Ruthenium Tetroxide Oxidation of Alkenes. A More Complete Picture
Albarella, Laura,Piccialli, Vincenzo,Sica, Donato,Smaldone, Dina
, p. 2442 - 2456 (2007/10/03)
The ruthenium tetroxide oxidation of some linear and cyclic alkenes, representatives of five substitution patterns, has been performed in acetone-water (5:1) solution at -70 deg C using stoichiometric ammounts of the oxidant.The main reaction products are 1,2-diols and/or α-ketols depending on the nature of the substrate little amounts of scission products, aldehydes and/or carboxylic acids, are also obtained.Generally 1,2-diols predominate over α-ketols except in the oxidation of (-)-α-pinene that afforded the α-ketol in 51percent yield while no trace of the corresponding 1,2-diol was detected.All reactions prceeded through the formation of unstable brownish precipitates, presumably the intermediate ruthenium (VI) esters, which easily decomposed during the work-up step.Results from oxidation of trans-7-tetradecene and cis and trans-11-tetradecenyl acetate indicated that the reaction was syn stereospecific.In some cases, 1,3-dioxolane products, formed by condensation of the 1,2-diol and the aldehyde materials, were also obtained among the reaction products.Their possible origin is briefly discussed.