HIGHLY SELECTIVE SYNTHESIS OF [(PERFLUOROALKYL)METHYL]OXIRANES (BY THE ADDITION OF IODOPERFLUOROALKANES TO ALLYL ACETATE)

Authors
CIRKVA V AMEDURI B BOUTEVIN B PALETA O
Citation
V. Cirkva et al., HIGHLY SELECTIVE SYNTHESIS OF [(PERFLUOROALKYL)METHYL]OXIRANES (BY THE ADDITION OF IODOPERFLUOROALKANES TO ALLYL ACETATE), Journal of fluorine chemistry, 83(2), 1997, pp. 151-158
Citations number
51
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Journal of fluorine chemistry → ACNP
ISSN journal
00221139
Volume
83
Issue
2
Year of publication
1997
Pages
151 - 158
Database
ISI
SICI code
0022-1139(1997)83:2<151:HSSO[(>2.0.ZU;2-T
Abstract
Mixtures of regioisomeric adducts of monoiodoperfluoroalkanes R-F-I (R -F = C4F9, C6F13 C8F17) with allyl acetate, RFCH2CHICH2OAc (1a-1c) and rearranged adducts RFCH2CH(OAc)-CH2I (2a-2c), were converted chemosel ectively to the corresponding oxiranes RFCH2CH(-O-)CH2 (3a-3c) in yiel ds of 94-96% (total yields of the two-step synthesis starting from R-F -I were 85-87%). The chemoselectivity of the oxirane formation appeare d to be very dependent on the solvent used. Dependence on the reaction conditions on formation of byproducts RFCH=CHCH2OAc (4a-4c) and RFCH= CHCH2OH (5a-5c) in the epoxidation reaction was studied. (C) 1997 Else vier Science S.A.