Sulphur-based directed benzylic metallations: lithiations of alkylarenesulphonates
Abstract
Benzylic anions (6) are obtained by regio-specific lithiations of ethyl 2-methylbenzenesulphonates. Evidence for the presence of the ethyl 2-lithiomethylbenzenesulphonates was obtained by efficient quenching studies with a range of electrophiles. Lithiations of the 2,4-dimethyl compound (9) gave the 2-lithiomethyl anion only, indicative of a predominant co-ordination mechanism in the lithiations.