New osmium-based reagent for the dihydroxylation of alkenes.
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.
Donohoe
Timothy J
TJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
Harris
Robert M
RM
Butterworth
Sam
S
Burrows
Jeremy N
JN
Cowley
Andrew
A
Parker
Jeremy S
JS
D000475:Alkenes / Q000737:chemistry*; D006900:Hydroxylation; D007202:Indicators and Reagents; D009992:Osmium / Q000737:chemistry*; D009993:Osmium Tetroxide / Q000737:chemistry
D000475:Alkenes; D007202:Indicators and Reagents; D009992:Osmium; D009993:Osmium Tetroxide