182805-17-0Relevant academic research and scientific papers
PARTICIPATION OF A NEIGHBORING AMIDE GROUP IN THE HYDROLYTIC C-OAr CLEAVAGE IN N-(ω-PHENOXYALKYL)AMIDES. PART II. N,N-BIS(2-PHENOXYETHYL)ACETAMIDE, N,N-BISACET- AND PROPIONAMIDES
Dobrzeniecka, Regina
, p. 515 - 523 (2007/10/02)
The hydrolysis rates of N,N-bis(2-phenoxyethyl)acetamide and the isomeric N,N-bisacet- and propionamides have been determined in a hydrochloric acid-dioxane solution in the range of 2.65-5.20 mole/dm3 at 94.6 deg C.In all cases the overall pseudo-first-order rate constant kobs = kA + kB, where kA is the rate constant for the formation of N,N-(bis(2-phenoxyethyl)amine A, while kB is the rate constant for the formation of 2-phenoxy-2'-hydroxydiethylamine B.It has been found that the alkyl group at the carbonyl carbon atom and the chlorine atom in the benzene ring have an influence on the overall rate of hydrolysis as well as on the proportion of products A and B.The values of the kB/kA ratio are higher in the case of propionamides, while the value of kB decreases in the following order para above ortho above meta for both series of the chloro substituted amides.
PARTICIPATION OF A NEIGHBORING AMIDE GROUP IN THE HYDROLYTIC C-OAr CLEAVAGE OF N-(ω-PHENOXYALKYL)AMIDES. PART I. N,N-BIS(2-PHENOXYETHYL)PROPIONAMIDE
Dobrzeniecka, Regina
, p. 1135 - 1140 (2007/10/02)
The acid catalyzed hydrolysis of N,N-bis(2-phenoxyethyl)propionamide has been made at 74.8, 84.5 and 94,5 deg C, yielding both bis(2-phenoxyethyl)amine (A) and N,N-(2-phenoxy-2'-hydroxy)diethylamine (B) and phenol.The assistance from the amido group in a displacement of phenol was observed.Kinetic studies have been used to analyze the pathway.The results show that both the amines are formed in two parallel reactions of pseudo-first-order rate constants with kB/kA = 1.20 - 1.77 at 94.5 deg C depending on the concentration of hydrochloric acid.
