Soft stereoelectronic effects at carboxyl oxygen

BM Tadayoni, J Huff, J Rebek Jr

Index: Tadayoni, B. Mitra; Huff, Jeffrey; Rebek Jr., Julius Journal of the American Chemical Society, 1991 , vol. 113, # 6 p. 2247 - 2253

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Citation Number: 10

Abstract

Abstract: The effects of lone pair basicity at carboxyl oxygen were examined in the context of intramolecular general-base catalysis (igbc) of enolization of ketones. Molecules synthesized from Kemp triacid units and xanthene-l, 8-dicarboxylic acid were constructed in such a way that the more basic syn lone pair of a carboxylate is directed toward the a- hydrogen of an enolizable ketone. For the Kemp triacid molecules, in which an 1 1'/2- ...