Alkylphenylacetylenes, C6H5CCCH2R, have been metallated at the propargylic positions with an excess of n-butyllithium in diethyl ether at 0°C. Mono- and di-silyl derivatives have been isolated by quenching the metallation mixtures with Me3SiCl at different times. Pseudo-first order rate constants have been calculated for the monometallation from the rate of formation of the silylated products. A Taft correlation gives ρ* = 1.8.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
- Materials Chemistry