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 d...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
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2006
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| _version_ | 1826274599706296320 |
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| author | Donohoe, T Harris, R Butterworth, S Burrows, J Cowley, A Parker, J |
| author_facet | Donohoe, T Harris, R Butterworth, S Burrows, J Cowley, A Parker, J |
| author_sort | Donohoe, T |
| collection | OXFORD |
| description | 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. |
| first_indexed | 2024-03-06T22:45:54Z |
| format | Journal article |
| id | oxford-uuid:5d2a611c-65d5-44a5-8ded-213f0ed59caf |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:45:54Z |
| publishDate | 2006 |
| record_format | dspace |
| spelling | oxford-uuid:5d2a611c-65d5-44a5-8ded-213f0ed59caf2022-03-26T17:32:41ZNew osmium-based reagent for the dihydroxylation of alkenes.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:5d2a611c-65d5-44a5-8ded-213f0ed59cafEnglishSymplectic Elements at Oxford2006Donohoe, THarris, RButterworth, SBurrows, JCowley, AParker, JThe 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. |
| spellingShingle | Donohoe, T Harris, R Butterworth, S Burrows, J Cowley, A Parker, J New osmium-based reagent for the dihydroxylation of alkenes. |
| title | New osmium-based reagent for the dihydroxylation of alkenes. |
| title_full | New osmium-based reagent for the dihydroxylation of alkenes. |
| title_fullStr | New osmium-based reagent for the dihydroxylation of alkenes. |
| title_full_unstemmed | New osmium-based reagent for the dihydroxylation of alkenes. |
| title_short | New osmium-based reagent for the dihydroxylation of alkenes. |
| title_sort | new osmium based reagent for the dihydroxylation of alkenes |
| work_keys_str_mv | AT donohoet newosmiumbasedreagentforthedihydroxylationofalkenes AT harrisr newosmiumbasedreagentforthedihydroxylationofalkenes AT butterworths newosmiumbasedreagentforthedihydroxylationofalkenes AT burrowsj newosmiumbasedreagentforthedihydroxylationofalkenes AT cowleya newosmiumbasedreagentforthedihydroxylationofalkenes AT parkerj newosmiumbasedreagentforthedihydroxylationofalkenes |