1783-36-4Relevant articles and documents
Amidines. Part 39.1 Formation of N1,N1-dialkylamidines in the reaction between amide acetals and substituted anilines in pyridine. Reaction mechanisms
Oszczapowicz, Janusz,Osek, Jerzy
, p. 1919 - 1923 (2007/10/03)
The reaction rates of six N,N-dialkylformamide acetals (R1)2N-CH(OR2)2, with a series of anilines substituted on the phenyl ring have been measured in pyridine. The reaction is found to be irreversible and obeys second-order kinetics. Reaction rates are correlated with Hammett σ constants. Based on the plots and a comparison of reaction rate constants it is shown that the reaction proceeds via two mechanisms which differ from that for the reaction in neutral solvents. It is shown that for compounds with weakly basic NH2 groups the reaction rates in pyridine are markedly higher than in neutral solvents.
Amidines. Part 20. Rate of Reaction of N,N-Dialkylformamide Acetals with Substituted Anilines
Osek, Jerzy,Oszczapowicz, Janusz,Drzewinski, Witold
, p. 1961 - 1964 (2007/10/02)
Rate of reaction of seven N,N-dialkylformamide acetals R2N-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 ? constants for substituents on the phenyl ring of the aniline molecule.On the basis of the kinetic data, the mechanism of reaction is discussed.
STEREOSPECIFIC FORMATION OF AMIDINES BY 1,1-ADDITION OF AMINES TO ISOCYANIDES
Hegarty, Anthony F.,Chandler, Anne
, p. 885 - 888 (2007/10/02)
Addition of secondary amines to isonitriles in the presence of AgCl at low temperature gives isolable but thermodynamically unstable Z-amidines; only the more stable 6E undergoes ring expansion to the imidazoline 7.
