ORGN 155 |
| Epoxides are known for their chemical utility but are equally significant as a protecting group for olefins. Deprotection of the epoxide to the parent alkene has been demonstrated with several low-valent metals by reductive deoxygenation. For example, ZrCl4/NaI and Mo(CO)6 reagents promote deoxygenation of epoxides to alkenes. In addition, epoxides having alkyl, aryl, ether, carbonyl, and hydroxyl functional groups α or β to the oxirane ring were tolerant of the deoxygenation. Furthermore, in the case of zirconium high stereospecificity has been observed. During the investigation of the synthetic utility of NbCl3(DME), we discovered that upon addition of an epoxide to the niobium(III) complex, the corresponding alkene was produced. This discovery has led us to examine the scope and limitations associated with niobium(III) and its deoxygenative effect upon structurally diverse epoxides.
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Process R&D, Physical Organic Chemistry, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |
