Metal ion effects in intramolecular reactions. Effects of divalent metal ions on intramolecular acetamido group participation in ester hydrolysis

TH Fife, TJ Przystas, MP Pujari

Index: Fife, Thomas H.; Przystas, Theodore J.; Pujari, Mahesh P. Journal of the American Chemical Society, 1988 , vol. 110, p. 8157 - 8163

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Citation Number: 11

Abstract

Abstract: The hydrolysis reactions of a series of esters of a-acetamidocinnamic acid proceed with formation of an oxazolinone intermediate. In 50% dioxane-H20 (v/v) at 50" C, an oxazolinone can be observed spectrophotometrically in the OH--catalyzed cyclization reactions of the a-acetamido-substituted esters with leaving groups of pKa 12.4 or less. In comparison with the OH--catalyzed hydrolysis of the corresponding cinnamate esters, the ...