Journal of Fluorine Chemistry p. 151 - 158 (1997)
Update date:2022-08-11
Topics:
Cirkva, Vladimir
Ameduri, Bruno
Boutevin, Bernard
Paleta, Oldrich
Mixtures of regioisomeric adducts of monoiodoperfluoroalkanes RF-I (RF = C4F9, C6F13, C8F17) with allyl acetate, RFCH2CHICH2OAc (1a-1c) and rearranged adducts RFCH2CH(OAc)-CH2I (2a-2c), were converted chemoselectively to the corresponding oxiranes RFCH2CH(-O-)CH2 (3a-3c) in yields of 94-96% (total yields of the two-step synthesis starting from RF-I were 85-87%). The chemoselectivity of the oxirane formation appeared 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.
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