65608-93-7Relevant academic research and scientific papers
An iron-catalysed synthesis of amides from nitriles and amines
Allen, C. Liana,Lapkin, Alexei A.,Williams, Jonathan M.J.
experimental part, p. 4262 - 4264 (2009/10/26)
The cheap, commercially available iron complex, Fe(NO3)3·9H2O, has been used to catalyse the formation of amides by the addition of amines to nitriles.
Kinetics and mechanism of the aminolysis of thiophenyl methylacetates in acetonitrile
Oh, Hyuck Keun,Yang, Jin Hee,Cho, In Ho,Lee, Hai Whang,Lee, Ikchoon
, p. 485 - 490 (2007/10/03)
The aminolysis of Z-thiophenyl methylacetates (C2H5C(double bond O)SC6H4Z) with X-benzylamines in acetonitrile has been investigated at 45 °C. The reaction is found to proceed by a stepwise mechanism in which the rate-determining step is the breakdown of the zwitterionic tetrahedral intermediate, T±, with possibly a hydrogen-bonded four-center-type transition state. These mechanistic conclusions are drawn based on (i) the large magnitude of βX (= 1.2 to approximately 2.5) and βz (= -0.9 to approximately -1.5), (ii) the normal kinetic isotope effects (kH/kD?1.2) involving deuterated benzylamines (XC6H4CH2ND2), (iii) a large positive ρxz (= 2.4) and (iv) adherence to the reactivity-selectivity principle in all cases. The extremely large βX (βnuc) values can be accounted for by the loss of a strong localized cationic charge on the N atom of benzylamines in the expulsion from the T±. The pKa° (≥10.0) is high due to a large ratio of the expulsion rates of the amine (k-a) to thiophenolate (kb) (k-a/kb) from the T±.
Highly selective amidation of benzylic alcohols with nitriles. A modified ritter reaction
Firouzabadi,Sardarian,Badparva
, p. 601 - 607 (2007/10/02)
Benzyl alcohols react selectively with different nitriles in the presence of a catalytic amount of boron trifluoride and produce amides in high yields. Deactivated p-nitrobenzyl, allylic, primary, secondary, and tertiary saturated alcohols do not react.
