Facile dihydroboration of 1-trimethylgermyl-1-alkynes with 9-borabicyclo[3.3.1]nonane (9-BBN) followed by oxidation

ORGN 394

Narayan G. Bhat, nbhat@panam.edu1, Robert L. Salazar2, and Aroldo J. Ibarra2. (1) Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541, (2) Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541
1-Trimethylgermyl-1-alkynes easily prepared by the deprotonation of the terminal alkynes with n-butyllithium followed by reaction with trimethylgermanium bromide readily undergo dihydroboration with 9-borabicyclo[3.3.1]nonane (9-BBN) in tetrahydrofuran at room temperature for 12 hours. The resulting dihydroborated products are reacted with alkaline hydrogen peroxide at 0oC followed by stirring at room temperature for 4 hours to provide the corresponding alpha-trimethylgermyl -1-alkanols in excellent yields (82%-92%). The structures of these alpha-trimethylgermyl-1-alkanols are confirmed by PMR and CMR spectral data.

 

Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005