Physical properties and synthetic utility of. alpha.-alkoxyorganolithium species as studied through ligand selectivity in tin-lithium exchange

JS Sawyer, A Kucerovy, TL Macdonald…

Index: Sawyer,J.S.; Kucerovy,A.; Macdonald,T.L. Journal of the American Chemical Society, 1988 , vol. 110, p. 842

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Citation Number: 117

Abstract

Abstract: The effects of alkoxy substitution on tetrahedral carbanions were studied by examining ligand selectivity in the tin-lithium exchange reaction in the corresponding stannanes. The thermodynamic stability of the derived organolithium species was studied by competitive exchange experiments and low-temperature NMR to reveal an order of decreasing stability as follows: R'OCH2Li> R10CH (R2) Li> MeLi> RLOCR2R3Li> n-BuLi ...