Reactions of N-sulfinylfluoroalkanesulfonylamides with alkene oxides

Article abstract of DOI:10.1016/0022-1139(96)03467-7

Reactions of N-sulfinylfluoroalkanesulfonylamides, R_fSO₂NSO (1), with alkene oxides 2 at room temperature gave the cyclo condensation products 2-oxa-3-fluoroalkanesulfonyl-1,2,3-oxathiazolidines, R_fSO₂NCH(R)CH₂OS(O) (3). When R was phenyl, the compound decomposed at 160 °C to give N-fluoroalkanesulfonylaziridine, R₁SO₂NCH₂CH(C₆H₅), with elimination of SO₂. Acidic hydrolysis of 3c [R_f=I(CF₂) ₂O(CF₂)₂, R=Ph] gave R_fSO₂NHCH(Ph)CH₂OH (5) which was identified by X-ray diffraction analysis.