1. Ring-Opening of Carbamate-Protected Aziridines and Azetidines in Liquid Sulfur Dioxide.
- Author
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Lugiņina, Jevgeņija, Uzuleņa, Jevgeņija, Posevins, Daniels, and Turks, Māris
- Subjects
- *
SULFUR dioxide , *CARBAMATES , *AZIRIDINES , *RING-opening reactions , *LEWIS acids , *SULFONAMIDES - Abstract
The reactions of halides or pseudohalides of group I and II metals with carbamate-protected aziridines and azetidines 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, carbamate-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 procedure occurred without racemization of the stereogenic centers. [ABSTRACT FROM AUTHOR]
- Published
- 2016
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