Structural effects on reactivity in intramolecular catalysis. The hydrolysis of N-alkylated monoamides derived from norbornene-2, 3-dicarboxylic acid

R Kluger, M Brandl

Index: Kluger, Ronald; Brandl, Michael Canadian Journal of Chemistry, 1984 , vol. 62, p. 2515 - 2520

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Abstract

Monoamides of 2, 3-endo-cis-5-norborene dicarboxylic acid (compounds 1-5) were prepared by addition of primary alkyl amines (n-propyl-, 2-methoxyethyl-, 2-fluoroethyl-, 2, 2- difluoroethyl-, 2, 2, 2-trifluoroethyl-) to 2, 3-endo-cis-5-norborene dicarboxylic anhydride. The rates of hydrolysis of each compound in solutions whose acid concentration ranged from 0.01 M to 9 M were determined. Rates increase with acidity above 0.1 M until a ...