Imine-forming elimination reactions. I. General base acid catalysis and influence of the nitrogen substituent on rates and equilibria for carbinolamine dehydration

JM Sayer, M Peskin, WP Jencks

文献索引：Sayer,J.M. et al. Journal of the American Chemical Society, 1973 , vol. 95, p. 4277 - 4287

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被引用次数: 91

摘要

Abstract: The base-catalyzed dehydration of carbinolamines derived from substituted hydrazines and p-chlorobenzaldehyde is strongly accelerated by electron-withdrawing substituents on the hydrazine moiety; the value of PN for the hydroxide ion catalyzed reaction is approximately-0.97. Electron withdrawal at nitrogen decreases the equilibrium constants for conversion of the carbinolamines to the hydrazones: PN=-0.4. The Bronsted ...