Deuterium isotope effects and the mechanism of kinetic enolate formation

HP Beutelman, L Xie…

Index: Beutelman, Hans P.; Xie, Linfeng; Saunders, William H. Journal of Organic Chemistry, 1989 , vol. 54, # 7 p. 1703 - 1709

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Citation Number: 21

Abstract

2-Methyl-3-pentanone, 2-methyl-3-pentanone-2-d, 2-methyl-3-pentanone-4, 4-d2, 3-methyl- 2-butanone, and 3-methyl-2-butanone-I, I, l-d3 have been treated with lithium dialkylamide bases (LDA, LDEA, and LTMP) in the dipolar aprotic solvents THF and DME, with and without added HMPA. Ratios of the product enolates were determined by quenching with trimethylsilyl chloride followed by GC analysis. Isotope effects calculated from these ...