M. Haddach et al., SYNTHESIS AND REACTIVITY OF NEW PERFLUOROALKYL SYNTHONS - ATYPICAL BEHAVIOR OF F-ALKYLATED AZIRINES AND AZIRIDINES, Tetrahedron, 49(21), 1993, pp. 4627-4638
F-alkyl chains perturb the reactivity of substrates in an often unpred
ictable way. F-alkyl azirine and aziridine carboxylates were prepared
from F-alkynylesters, in 80 and 60% yield, respectively, and were foun
d to display reactivities different from those of their hydrocarbon an
alogs. Thus, F-alkylazirines (5) give addition products easily but res
ist ring opening, while the F-alkylaziridines (8) are extremely stable
, both towards nucleophilic and electrophilic reagents and irrespectiv
e of the medium used, neutral, acid or basic.