The Journal of Organic Chemistry

Metal alkoxide modified organometallic reagents. Preparation and stability of organolithium reagents in tetrahydrofuran in the presence of magnesium 2- …

CG Screttas, BR Steele

Index: Screttas, Constantinos G.; Steele, Barry R. Journal of Organic Chemistry, 1989 , vol. 54, # 5 p. 1013 - 1017

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Citation Number: 34

Abstract

The metalating ability of alkyllithium reagents and their tendency to cleave THF are greatly diminished in the presence of magnesium 2-ethoxyethoxide, 1. Advantage may be taken of this to generate organolithium reagents in THF in the presence of 1 under conditions not normally favorable to their stability. Thus, by reaction with metallic lithium in the presence of 1 in THF, the compounds RX (R= n-Bu, s-Bu, t-Bu, cyclohexyl, menthyl, p-methoxyphenyl, ...