72024-59-0Relevant academic research and scientific papers
One-pot synthesis of carbamates and thiocarbamates from Boc-protected amines
Kim, Hee-Kwon,Lee, Anna
, p. 4890 - 4892 (2016/10/21)
A highly efficient one-pot procedure for the synthesis of carbamates and thiocarbamates has been described. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, the isocyanate intermediates were generated in situ for further reactions with alcohols and thiols to afford the desired carbamates and thiocarbamates in high yields.
Facile one-pot synthesis of unsymmetrical ureas, carbamates, and thiocarbamates from Cbz-protected amines
Kim, Hee-Kwon,Lee, Anna
supporting information, p. 7345 - 7353 (2016/08/05)
A novel one-pot synthesis of unsymmetrical ureas, carbamates and thiocarbamates from Cbz-protected amines has been developed. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, isocyanates are generated in situ, which facilitate rapid reaction with amines, alcohols, and thiols to afford the corresponding ureas, carbamates and thiocarbamates in high yields.
Kinetics and mechanism of the aminolysis of aryl N-benzyl thiocarbamates in acetonitrile
Oh, Hyuck Keun
experimental part, p. 137 - 140 (2011/11/01)
The aminolysis reactions of phenyl N-benzyl thiocarbamate with benzylamines in acetonitrile at 50.0 °C are investigated. The reactions are first order in both the amine and the substrate. Under amine excess, pseudo-first coefficient (kobs) are obtained, plot of kobs vs free amine concentration are linear. The signs of ρXZ (X and ρZ with respect to the sustituent in the substrate and large ρXZ value indicate that the reactions proceed concerted mechanism. The normal kinetic isotope effects (kH/k D = 1.3 ～ 1.5) involving deuterated benzylamine nucleophiles suggest a hydrogen-bonded, four-centered-type transition state. The activation parameters, ΔH?and AS?, are consistent with this transition state structure.
