847456-93-3Relevant academic research and scientific papers
Lithium diisopropylamide-mediated ortholithiations: Lithium chloride catalysis
Gupta, Lekha,Hoepker, Alexander C.,Singh, Kanwal J.,Collum, David B.
supporting information; experimental part, p. 2231 - 2233 (2009/08/07)
Ortholithiations of a range of arenes mediated by lithium diisopropylamide (LDA) in THF at -78 °C reveal substantial accelerations by as little as 0.5 mol % of LiCl (relative to LDA). Substrate dependencies suggest a specific range of reactivity within wh
n-Butyllithium/N,N,N',N'-tetramethylethylenediamine-mediated ortholithiations of aryl oxazolines: Substrate-dependent mechanisms
Chadwick, Scott T.,Ramirez, Antonio,Gupta, Lekha,Collum, David B.
, p. 2259 - 2268 (2007/10/03)
n-Butyllithium/N,N,N′,N′-tetramethylethylenediamine-mediated ortholithiations of aryloxazolines are described. Methyl substituents on the aryloxazoline and substituents at the meta position of the arenes (methoxy, oxazolinyl, and fluoro) influence the rates and the mechanisms. Monomer- and dimer-based reactions are implicated. Density functional calculations probe details of the mechanism and suggest the origins of cooperative effects in meta-substituted aryl oxazolines.
