With osmium

Another method for the hydroxylation of the etliylenic linkage consists in treatment of the alkene with osmium tetroxide in an inert solvent (ether or dioxan) at room temperature for several days an osmic ester is formed which either precipitates from the reaction mixture or may be isolated by evaporation of the solvent. Hydrolysis of the osmic ester in a reducing medium (in the presence of alkaline formaldehyde or of aqueous-alcoholic sodium sulphite) gives the 1 2-glycol and osmium. The glycol has the cis structure it is probably derived from the cyclic osmic ester ... 

The element forms an alloy with osmium which is used for tipping pens and compass bearings. 

With osmium tetroxide catalyst [PLATINUM-GROUP METALS, COMPOUNDS] (Vol 19)... 

CARBON - CARBON AND ARTIFICIALGRAPHITE - APPLICATIONS OF BAKED AND GRAPHITIZED CARBON] (Vol 4) -With osmium tetroxide catalyst [PLATINUM-GROUP METALS, COMPOUNDS] (Vol 19)... 

Fig. 1. Transmission electron micrograph of ABS produced by an emulsion process. Staining of the mbber bonds with osmium tetroxide provides contrast...

Cyclodecanediol has been prepared by the hydrogenation of sebacoin in the presence of Raney nickel or platinum, by the reduction of sebacoin with aluminum isopropoxide or lithium aluminum hydride, and by the oxidation of cyclodecene with osmium tetroxide and pyridine. ... 

A classical method for the vicinal hydroxylation of a double bond involves treatment with osmium tetroxide to give a cyclic ester, followed by reductive cleavage to the glycol ... 

Many of the reactions already discussed for the preparation of bis-oxygenated pregnanes can also be used for the synthesis of 17,20,21-tris-oxygenated pregnanes by proper choice of substrate. Thus, reaction of a 17-vinyl-17-hydroxy steroid or a A -21-hydroxypregnene with osmium tetroxide will give the 17,20,21-triol, and the Stork reaction can be applied to 17a-hydroxy-20-keto steroids. 

One reaction touched upon briefly in an earlier discussion is the hydroxyla-tion of a A -20-cyano steroid with osmium tetroxide. When a 21-acetoxyl group is also present, the important dihydroxyacetone side-chain is obtained ... 

Because the unsaturated nitrile does not react with osmium tetroxide as rapidly as a simple A holefin, selectivity between other unsaturated centers is difficult to achieve. 

Since electronegative groups at C-20 or C-21 deactivate a A hdouble bond towards attack by osmium tetroxide, Swiss workers have devised procedures wherein these groups are first reduced with lithium aluminum hydride, and the resulting aluminum complexes are then treated with osmium tetroxide... 

Selective hydroxylation with osmium tetroxide (one equivalent in ether-pyridine at 0 ) converts (27) to a solid mixture of stereoisomeric diols (28a) which can be converted to the corresponding secondary monotoluene-sulfonate (28b) by treatment with /7-toluenesulfonyl chloride in methylene dichloride-pyridine and then by pinacol rearrangement in tetrahydrofuran-lithium perchlorate -calcium carbonate into the unconjugated cyclohepte-none (29) in 41-48 % over-all yield from (27). Mild acid-catalyzed hydrolysis of the ketal-ketone (29) removes the ketal more drastic conditions by heating at 100° in 2 hydrochloric acid for 24 hr gives the conjugated diketone (30). 

Another important reaction associated with the name of Sharpless is the so-called Sharpless dihydroxylation i.e. the asymmetric dihydroxylation of alkenes upon treatment with osmium tetroxide in the presence of a cinchona alkaloid, such as dihydroquinine, dihydroquinidine or derivatives thereof, as the chiral ligand. This reaction is of wide applicability for the enantioselective dihydroxylation of alkenes, since it does not require additional functional groups in the substrate molecule ... 

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