title: n-Butyllithium/N,N,N',N'-tetramethylethylenediamine-mediated ortholithiations of aryl oxazolines: substrate-dependent mechanisms.
abstract: 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.
authors.affiliation: Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
authors.forename: Scott T
authors.initials: ST
authors.lastname: Chadwick
authors.forename: Antonio
authors.initials: A
authors.lastname: Ramirez
authors.forename: Lekha
authors.initials: L
authors.lastname: Gupta
authors.forename: David B
authors.initials: DB
authors.lastname: Collum
mesh_terms: D005029:Ethylenediamines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D005029:Ethylenediamines; D009942:Organometallic Compounds; D010080:Oxazoles; C005798:N,N,N',N'-tetramethylethylenediamine; D008094:Lithium