Ring-Opening of Carbamate-Protected Aziridines and Azetidines in Liquid Sulfur Dioxide
European Journal of Organic Chemistry 2016
Jevgeņija Lugiņina, Jevgeņija Uzuleņa, Daniels Posevins, Māris Turks

The reactions of halides or pseudohalides of group I and II metals with carbamate-protected aziridines and azet- idines in liquid sulfur dioxide as solvent resulted in the efficient ring-opening of these heterocycles. Sulfur dioxide, as a highly polar solvent, solubilizes the inorganic salts and acts as a mild Lewis acid to accelerate the ring-opening. For this reason, carb- amate-protected small heterocycles can be used instead of the corresponding sulfonamides, the activities of which are well- established in ring-opening reactions. Thiols also performed well in the SO2-assisted ring-opening of aziridines. This proce- dure occurred without racemization of the stereogenic centers.


Atslēgas vārdi
sulfur dioxide, aziridine ring opening, azetidine ring opening, solvent
DOI
10.1002/ejoc.201600141

Lugiņina, J., Uzuleņa, J., Posevins, D., Turks, M. Ring-Opening of Carbamate-Protected Aziridines and Azetidines in Liquid Sulfur Dioxide. European Journal of Organic Chemistry, 2016, Iss.9, 1760.-1771.lpp. e-ISSN 1099-0690. Pieejams: doi:10.1002/ejoc.201600141

Publikācijas valoda
English (en)
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