title: Sodium Diisopropylamide in N,N-Dimethylethylamine: Reactivity, Selectivity, and Synthetic Utility.
abstract: The reactivities and chemoselectivities of sodium diisopropylamide (NaDA) in N,N-dimethylethylamine (DMEA) are compared with those of lithium diisopropylamide (LDA) in tetrahydrofuran (THF). Metalations of arenes, epoxides, ketones, hydrazones, dienes, and alkyl and vinyl halides are represented. The positive attributes of NaDA-DMEA include high solubility, stability, resistance to solvent decomposition, and ease of preparation. The high reactivities and chemoselectivities often complement those of LDA-THF.
authors: Department of Chemistry and Chemical Biology, Cornell University , Baker Laboratory, Ithaca, New York 14853-1301, United States.
authors: Yun
authors: Y
authors: Ma
authors: Department of Chemistry and Chemical Biology, Cornell University , Baker Laboratory, Ithaca, New York 14853-1301, United States.
authors: Russell F
authors: RF
authors: Algera
authors: Department of Chemistry and Chemical Biology, Cornell University , Baker Laboratory, Ithaca, New York 14853-1301, United States.
authors: David B
authors: DB
authors: Collum
mesh_terms: D005021:Ethylamines / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008670:Metals / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry; D012995:Solubility; D012997:Solvents / Q000737:chemistry
chemical_list: D005021:Ethylamines; D005663:Furans; D008670:Metals; D011437:Propylamines; D012997:Solvents; C018674:tetrahydrofuran; C047305:N,N-dimethylethylamine; C007442:diisopropylamine