Amidines. Part 20. Rates of reaction of N,N-dialkylformamide acetals with substituted anilines

Abstract

Rates of reaction of seven N,N-dialkylformamide acetals R¹₂N–CH(OR²)₂ with a series of anilines substituted on the phenyl ring have been measured in benzene, methanol, chloroform, and tetrahydrofuran by use of a g.l.c. method. In each case studied reaction is irreversible and obeys a second-order kinetic equation. Reaction rates correlate with Hammett σ constants for substituents on the phenyl ring of the aniline molecule. On the basis of the kinetic data, the mechanism of reaction is discussed.