The mechanism of solvolysis of 2-halogenoalkylsilanes. Part II. Deuterium isotope effects
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 746-748
- https://doi.org/10.1039/j29700000746
Abstract
The compounds Me3Si·CH2·CD2Br, Me3Si·CHD·CH2Br, and (CD3)2MeSi·CH2·CH2Br have been prepared and their solvolysis rates in aqueous ethanol have been determined and compared with those for the non-deuteriated compounds. The acid-catalysed solvolysis of the 2-hydroxyalkylsilanes is similar to the solvolysis of 2-halogenoalkylsilanes and it appears likely that it follows a similar mechanism. The compound Me3Si·CH2·CD2·OH was prepared and its rate of solvolysis was determined and compared with that of the non-deuteriated material in the same medium. The mechanism of the solvolysis reaction is discussed in the light of the observed isotope effects and the stereochemical evidence reported previously.Keywords
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