Ezzat Khan, R. Kempe, B. Wrackmeyer
Mar 1, 2009
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0
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Journal
Applied Organometallic Chemistry
Abstract
The reaction of alkyn-1-yl(chloro)(methyl)vinyl- and alkyn-1-yl(chloro)(phenyl)-vinylsilane with 9-borabicyclo[3.3.1]nonane (9-BBN) afforded selectively 1-silacyclopent-2-ene derivatives containing a SiCl function, as a result of consecutive 1,2-hydroboration and 1,1-organoboration. Protodeborylation with acetic acid left the SiCl functions in various 1-silacyclopent-2-enes untouched, whereas acetic acid in the presence of dipropylamine led to conversion of the SiCl into the SiOAc function. New starting materials and all products were characterized in solution by multinuclear NMR spectroscopy (1H, 11B, 13C and 29Si NMR), and the molecular structures of two 1-silacyclopent-2-ene derivatives were determined by X-ray analysis. The gas phase geometries of 1-silacyclopent-2-enes were optimized by DFT calculations [B3LYP/6-311 + G(d,p) level of theory], found to be in reasonable agreement with the results of the crystal structure determination, and NMR parameters were calculated at the same level of theory. Copyright © 2009 John Wiley & Sons, Ltd.