Method of Continuous Variation: Characterization of Alkali Metal Enolates Using ¹H and ¹⁹F NMR Spectroscopies

Abstract

The method of continuous variation in conjunction with (1)H and (19)F NMR spectroscopies was used to characterize lithium and sodium enolates solvated by N,N,N',N'-tetramethylethyldiamine (TMEDA) and tetrahydrofuran (THF). A strategy developed using lithium enolates was then applied to the more challenging sodium enolates. A number of sodium enolates solvated by TMEDA or THF afford exclusively tetramers. Evidence suggests that TMEDA chelates sodium on cubic tetramers.