ORGN 183 |
| A series of anodic coupling reactions have been studied in order to probe the effect of polarization on carbon-carbon bond formation. Experimental evidence suggests that it is the polarization of the radical cation intermediate in an oxidative cyclization that governs carbon-carbon vs. carbon oxygen bond formation and not the electron-richness of the radical cation as thought earlier. For ene diol ether type substrates, the reactions are only successful when the second oxygen substituents on the initiating olefin either increase or maintains the polarization of the radical cation. A reaction using an alkyl substituted enol ether initiating group was intriguing in that it led to the formation of highly functionalized bicyclic molecules containing four contiguous stereogenic atoms, one of which was quaternary.
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Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster
Sci-Mix
Division of Organic Chemistry |
