ORGN 96

Highly diastereoselective synthesis of (E)-1-bromo-1-trimethylgermyl-1-alkenes via the hydroalumination of 1-trimethylgermyl-1-alkynes followed by the reaction with N-bromosuccinimide

Narayan G. Bhat, nbhat@panam.edu, Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541 and Robert L. Salazar, Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541.

A highly diastereoselective synthesis of (E)-1-bromo-1-trimethylgermyl-1-alkenes via the hydroalumination of the corresponding 1-trimethylgermyl-1-alkynes with diisobutylaluminum hydride (DIBAL-H) in dichloromethane followed by bromination with N-bromosuccinimide is presented. 1-Trimethylgermyl-1-alkynes (easily prepared by the deprotonation of the corresponding alkynes followed by germylation with trimethylgermyl bromide) smoothly undergo hydroalumination with DIBAL-H in dichloromethane at room temperature for 16 h. The bromination of the resulting intermediates with N-bromosuccinimide in tetrahydrofuran at 0 ^oC provides the corresponding (E)-1-bromo-1-trimethylgermyl-1-alkenes in good yields (78%-86%) and in high stereochemical purities (> 98%).

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005