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1970•Journal of the Chemical Society B Physical OrganicRequires access

The mechanism of solvolysis of 2-halogenoalkylsilanes. Part II. Deuterium isotope effects

A.W.P. Jarvie, A. Holt, John T. Thompson

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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.

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What this paper is about

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.

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Available 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.

Key concepts: Solvolysis, Chemistry, Kinetic isotope effect, Deuterium, Aqueous solution, Ethanol, Medicinal chemistry, Organic chemistry

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