34889-53-7Relevant academic research and scientific papers
N-Tosylaziridine, a new substrate for chemical fixation of carbon dioxide via ring expansion reaction under atmospheric pressure
Sudo, Atsushi,Morioka, Yosuke,Sanda, Fumio,Endo, Takeshi
, p. 1363 - 1365 (2004)
N-Tosylaziridine was found to be a useful substrate for cycloaddition reaction with carbon dioxide. The reaction was successfully catalyzed by lithium bromide under atmospheric pressure to give the corresponding five-membered cyclic urethane, N-tosyl-1,3-oxazolidin-2-one, selectively. It was found that electron-donating nature of the substituent at 2-position of N-tosylaziridine accelerated the reaction, and this tendency allowed us to estimate the reaction mechanism.
Cycloaddition of CO2 to challenging N-tosyl aziridines using a halogen-free niobium complex: Catalytic activity and mechanistic insights
Arayachukiat, Sunatda,Yingcharoen, Prapussorn,Vummaleti, Sai V.C.,Cavallo, Luigi,Poater, Albert,D'Elia, Valerio
, p. 280 - 285 (2017)
An efficient and facile approach to the regioselective synthesis of N-tosyloxazolidinones from the corresponding N-tosylaziridines and CO2 was developed using dual catalytic systems involving an early transition metal coordination compound as a Lewis acid and a nucleophilic cocatalyst. Among the screened Lewis acids, halogen-free niobium pentaethoxide (Nb(OEt)5) displayed the best catalytic activity when used in the presence of tetrabutylammonium iodide (TBAI). Systematic DFT calculations, supported by catalytic experiments, demonstrate that CO2 insertion is the rate determining step for this process and it is highly dependent on the steric hindrance at the niobium center.
Chemistry of Sulfonyl Isocyanates and Sulfonyl Isothiocyanates. XI. Cyclizations with Epoxides
McFarland, J. W.,Beaulieu, J. J.,Arrey, L. N.,Frey, L. M.
, p. 1431 - 1434 (2007/10/02)
4-Toluenesulfonyl isocyanate cyclized with 1,2-epoxy-3-phenoxypropane and 2,3-epoxypropyl 4-methoxyphenyl ether, respectively, to give 3-(4-toluenesulfonyl)-5-phenoxymethylene-2-oxazolidone (I) and 3-(4-toluenesulfonyl)-5-(4-methoxyphenoxymethylene)-2-oxazolidone (II).Compounds I and II were hydrolyzed in 2 M sodium hydroxide solution to the corresponding uncyclized hydroxy amides, VII and VIII.Compound I was remarkably stable toward 6M hydrochloric acid and amines.Styrene oxide, 1,2-epoxybutane, 3-chloro-1,2-epoxypropane, and 1-methoxy-2-methylpropylene oxide reacted with the isocyanate to afford 3-(4-toluenesulfonyl)-4-phenyl-2-oxazolidone (III), 3-(4-toluenesulfonyl)-4-ethyl-2-oxazolidone (IV), 3-(4-toluenesulfonyl)-5-chloromethyl-2-oxazolidone (V), and 3-(4-toluenesulfonyl)-4,4-dimethyl-5-methoxy-2-oxazolidone (VI), respectively.The yield of VI was constant over a temperature range of 25-90 deg.
