A rapid injection NMR study of the reaction of organolithium reagents with esters, amides, and ketones.

Abstract

Unexpectedly high rates of reaction between alkyllithium reagents and amides, compared to esters and ketones, were observed by Rapid Inject NMR and competition experiments. Spectroscopic investigations with 4-fluorophenyllithium (ArLi, mixture of monomer and dimer in THF) and a benzoate ester identified two reactive intermediates, a homodimer of the… (More)
DOI: 10.1021/acs.orglett.5b00650

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