ORGN 478 |
| Christos Kaimakliotis, Anthony O'Brien, Jovan Alston, Albert J. Fry, and Latorya Hicks. Department of Chemistry, Wesleyan University, Middletown, CT 06459 |
| The anodic oxidation of alpha-dimethylsilyl-beta-phenyl esters and the simpler substance 1-phenyl-2-trimethylsilylethane takes place at potentials which are much more positive than those of silanes not bearing a phenyl substituent. We have called this phenomenon the “anodic gamma-silyl effect”. We have postulated that the effect arises through an antibonding interaction between the rear lobe of the carbon-silicon sp3 orbital and the pi-system of the benzene ring. We will describe the evidence for this interpretation, its stereoelectronic implications and a stereochemical test of it, and a search for the corresponding gamma effects with germanium and tin. |
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Synthetic Organic Electrochemistry
9:00 AM-11:30 AM, Wednesday, September 10, 2003 Sheraton New York -- Royal Ballroom A, Oral
Division of Organic Chemistry |