ORGN 312 |
| James E. Johnson1, Debra D. Dolliver2, Lonchun Yu1, Diana C. Canseco1, Michael A. McAllister3, and Jeffrey E. Rowe4. (1) Department of Chemistry and Physics, Texas Woman's University, P.O.Box 425859, Denton, TX 76204, (2) Department of Chemistry & Physics, Southeastern Louisiana University, SLU 10878, Hammond, LA 70402, (3) Department of Chemistry, University of North Texas, Denton, TX 76203, (4) Department of Chemistry, La Trobe University, Bundoora, Victoria, Australia |
| Kinetic and stereochemical studies have been carried out on the reactions of the Z and E isomers of O-methylbenzohydroximoyl halides [ArC(X)=NOMe, X=F, Cl, and Br] with sodium methoxide in 9:1 DMSO-methanol. The reactions of methoxide ion with hydroximoyl fluorides (X=F) are stereospecific (retention of configuration). The experimental observations are consistent with a mechanism proceeding through a tetrahedral intermediate. Ab initio calculations were carried out to help explain the stereospecificity of these reactions.
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Physical Organic, Combinatorial, Materials, Molecular Recognition
8:00 PM-10:00 PM, Tuesday, March 30, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry |