Abstract
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 language | English |
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Pages (from-to) | 247-252 |
Number of pages | 6 |
Journal | Journal of Organometallic Chemistry |
Volume | 118 |
Issue number | 3 |
DOIs | |
State | Published - 12 Oct 1976 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
- Materials Chemistry