Novel synthesis of gem-dimetalloalkanes containing boron and silicon via the hydroboration of (Z)-1-trimethylsilyl-1-alkenes with dichloroborane-dioxane complex

ORGN 97

Narayan G. Bhat, nbhat@panam.edu1, Mary A. Villanueva2, and Yvette L. Clancy2. (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
(Z)-1-Trimethylsilyl-1-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyl-1-alkynes with dicylcohexylborane followed by protonolysis with acetic acid, readily react with dichloroborane-dioxane complex in dichloromethane at room temperature for 8 h. The resulting solution is then treated with 1,3-propane diol at 0 oC for half an hour to provide the corresponding gem-dimetalloalkanes containing boron and silicon. These alpha-trimethylsilylalkylboronate esters are purified by vacuum distillation in high yields (74%-86%) and the structures of these novel intermediates are further confirmed by selective oxidation with alkaline hydrogen peroxide to provide the corresponding alcohols containing trimethylsilyl group.
 

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