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Competitive formation of azetidinium pyrrolidinium and aziridinium ions during the fluorination of certain di o mesylated dimethylaminopentofuranosides

Competitive formation of azetidinium pyrrolidinium and aziridinium ions during the fluorination of certain di o mesylated dimethylaminopentofuranosides

Tetrahedron 48(29): 6033-6042

5-O-mesylated furanosides such as 3-dimethylamino-D-xylo (2.beta. and 10.beta.) or 2-dimethylamino-D-arabino (1.alpha., 7.alpha. and 7.beta.) readily afford a new class of bicyclic compounds with an azetidinium or a pyrrolidinium ring; whenever competitive aziridinium ion can be obtained (in the case of 3,5 or 2,5 dimesylates), formation of four or five-membered ring is mainly observed: these ions seem quite unreactive towards fluorinating agents.

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