ORGN 539 |
| The mechanism of the permanganate oxidation of 1,5-dienes was investigated by density functional theory calculations (B3LYP/6-311+G*). The experimentally observed (unexpected) products, 2,5-bis(hydroxymethyl) substituted tetrahydrofurans, are formed in a concerted reaction, which explains the observed stereoselectivity of the reaction. Water plays an important role in the reaction mechanism by significantly lowering the activation energies. |
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Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |