SYNTHESIS AND REACTIVITY OF NEW PERFLUOROALKYL SYNTHONS - ATYPICAL BEHAVIOR OF F-ALKYLATED AZIRINES AND AZIRIDINES

Authors
HADDACH M PASTOR R RIESS JG
Citation
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
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
21
Year of publication
1993
Pages
4627 - 4638
Database
ISI
SICI code
0040-4020(1993)49:21<4627:SARONP>2.0.ZU;2-G
Abstract
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.