Metallation-silylation and kinetic studies of arylmethylacetylenes

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15 Scopus citations


Arylmethylacetylenes, XC6H4CCCH3, have been metallated with an excess of n-butyllithium in diethyl ether at 0°C. By quenching the metallation mixtures with trimethylchlorosilane at different times, mono-, di- and tri-silyl derivatives have been isolated. Pseudo-first order rate constants for the monometallation were calculated from the rate of formation of the silylated products. A Hammett plot gave ρ{variant} = 1.3, indicating moderate delocalization into the aromatic ring, of the negative charge developed at the propargylic carbon during the metallation.

Original languageEnglish
Pages (from-to)247-252
Number of pages6
JournalJournal of Organometallic Chemistry
Issue number3
StatePublished - 12 Oct 1976

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry


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