Issue 7, 1973

Strain effects in acyl transfer reactions. Part II. The kinetics of aminolysis of some N-aryl-lactams

Abstract

The reactions between aliphatic amines and 1-p-nitrophenylazetidin-2-one (I) show marked general base catalysis while hydroxide ion catalysis becomes dominant at high pH. The effect of strain in the β-lactam is manifest in the overall rate of reaction of piperidine with (I) which is at least 103 times greater than that with the corresponding γ-lactam (II). The Brønsted coefficient of 1·05 for the uncatalysed reactions of (I) with alkylamines shows that the transition state for these reactions is advanced along the reaction co-ordinate as a result of this ring strain and involves less C–N bond stretching than expected for the aminolysis of unstrained anilides.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1973, 981-985

Strain effects in acyl transfer reactions. Part II. The kinetics of aminolysis of some N-aryl-lactams

G. M. Blackburn and J. D. Plackett, J. Chem. Soc., Perkin Trans. 2, 1973, 981 DOI: 10.1039/P29730000981

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