title: New osmium-based reagent for the dihydroxylation of alkenes.
abstract: The cis dihydroxylation of alkenes is most efficiently accomplished by reaction with osmium tetroxide. Recently, the expense and toxicity of osmium tetroxide have led to a number of attempts to harness alternative osmium-based reagents, including microencapsulation and solid support techniques. We describe here the development of a new nonvolatile, stable, and recoverable osmium-based reagent devised for the stoichiometric cis dihydroxylation of alkenes. Although attempts to make this new dihydroxylation work with catalytic amounts of this reagent were unsuccessful, we did develop a sensitive test for free osmium tetroxide leached from the reagent in situ: this test may well have uses in probing future applications of derivatized osmium reagents.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Donohoe
authors.forename: Robert M
authors.initials: RM
authors.lastname: Harris
authors.forename: Sam
authors.initials: S
authors.lastname: Butterworth
authors.forename: Jeremy N
authors.initials: JN
authors.lastname: Burrows
authors.forename: Andrew
authors.initials: A
authors.lastname: Cowley
authors.forename: Jeremy S
authors.initials: JS
authors.lastname: Parker
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D006900:Hydroxylation; D007202:Indicators and Reagents; D009992:Osmium / Q000737:chemistry*; D009993:Osmium Tetroxide / Q000737:chemistry
chemical_list: D000475:Alkenes; D007202:Indicators and Reagents; D009992:Osmium; D009993:Osmium Tetroxide