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Synthesis and molecular structures of 1-chloro-1-silacyclopent-2-enes. Combination of 1,2-hydroboration, 1,1-organoboration and protodeborylation

✍ Scribed by Ezzat Khan; Rhett Kempe; Bernd Wrackmeyer

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
199 KB
Volume
23
Category
Article
ISSN
0268-2605

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✦ Synopsis

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 SiCl function, as a result of consecutive 1,2‐hydroboration and 1,1‐organoboration. Protodeborylation with acetic acid left the SiCl functions in various 1‐silacyclopent‐2‐enes untouched, whereas acetic acid in the presence of dipropylamine led to conversion of the SiCl into the SiOAc function. New starting materials and all products were characterized in solution by multinuclear NMR spectroscopy (^1^H, ^11^B, ^13^C and ^29^Si 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.

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