Structures of three lithium ester enolates by X-ray diffraction: derivation of reaction path for cleavage into ketene and alcoholate

D Seebach, R Amstutz, T Laube…

Index: Seebach, Dieter; Amstutz, Rene; Laube, Thomas; Schweizer, W. Bernd; Dunitz, Jack D. Journal of the American Chemical Society, 1985 , vol. 107, # 19 p. 5403 - 5409

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Citation Number: 146

Abstract

Abstract: Crystal structure analyses have been carried out for lithium enolates of the following three esters: tert-butyl propionate ((Z)-1), tert-butyl2-methylpropionate (2), and methyl 3, 3-dimethylbutanoate ((Z)-3). Enolates (Z)-1 and 2 are dimeric (with one TMEDA per Li atom), whereas (2)-3 is tetrameric (with one THF per Li atom). The Z configuration of 1 and 3 established by X-ray analysis is in agreement with that assigned by Ireland. From a ...

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