Hydroalumination of (Z)-1-trimethylgermyl-1-alkenes followed by selective iodinolysis

ORGN 135

Narayan G. Bhat, nbhat@panam.edu, Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541 and Marivel Martinez, Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541.
A highly regioselective synthesis of 1-iodoalkyltrimethylgermanes is presented. (Z)-Trimethylgermyl-1-alkenes (easily prepared by the hydrozirconation of the corresponding 1-trimethylgermyl-1-alkynes followed by protonolysis) smoothly undergo hydroalumination with diisobutylaluminum hydride (DIBAL-H) in hexanes at room temperature for 16 h. The selective iodinolysis of the resulting intermediates with iodine at 0 oC for an hour provides the corresponding 1-iodoalkyltrimethylgermanes in high yields (72%-84%). The structures of these intermediates are confirmed by PMR and CMR spectral data.

 

Process R&D, Physical Organic Chemistry, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007