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N-Tosylaziridine, a new substrate for chemical fixation of carbon dioxide via ring expansion reaction under atmospheric pressure
Authors:Atsushi Sudo  Fumio Sanda
Affiliation:a Molecular Engineering Institute, Kinki University, 11-6 Kayanomori, Iizuka, Fukuoka 820-8555, Japan
b Chemical Resources Laboratory, Tokyo Institute of Technology, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8503, Japan
c Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Yoshida-honmachi, Sakyo-ku, Kyoto 606-8501, Japan
d Department of Polymer Science and Engineering, Faculty of Engineering, Yamagata University, Jonan, Yonezawa, Yamagata 992-8510, Japan
Abstract: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.
Keywords:Aziridine   Cycloaddition   Carbon dioxide   Atmospheric pressure   Carbon disulfide
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