65608-86-8Relevant academic research and scientific papers
Synthesis and application of a new fluorous-tagged ammonia equivalent
Nielsen, Simon D.,Smith, Garrick,Begtrup, Mikael,Kristensen, Jesper L.
supporting information; experimental part, p. 4557 - 4566 (2010/08/20)
A novel fluorous-tagged ammonia equivalent has been developed. It is based on a nitrogen-oxygen bond, which can be cleaved in a traceless manner by a molybdenum complex or samarium diiodide. The application in the synthesis of ureas, amides, sulfonamides, and carbamates is described. The scope of the fluo-rous N-O linker is exemplified by the synthesis of itopride, a drug used for the treatment of functional dyspepsia. Itopride was synthesized with the aid of fluorous purification methods and the product was isolated in good overall yield, with high purity.
Kinetics and mechanism of the aminolysis of aryl N-ethyl thiocarbamates in acetonitrile
Oh, Hyuck Keun,Park, Jie Eun,Sung, Dae Dong,Lee, Ikchoon
, p. 9285 - 9288 (2007/10/03)
The aminolysis of aryl N-ethyl thiocarbamates (EtNHC(=O)SC 6H4Z) with benzylamines (XC6H 4-CN2NH2) in acetonitrile at 30.0 °C is investigated. The rates are faster than the corresponding values for aryl N-phenyl thiocarbamates (PhNHC(=O)SC6H4Z), reflecting a stronger push to expel the leaving group by EtNH than the PhNH nonleaving group in a concerted process. The negative ρXZ (-0.86) and failure of the reactivity-selectivity principle found are consistent with the concerted mechanism. The kinetic isotope effects involving deuterated nucleophiles (k H/kD = 1-5-1.7) and low ΔH? with large negative ΔS? values suggest a hydrogen bond cyclic transition state.
