What is it about?
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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Why is it important?
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.
Perspectives
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.
Dr Vladimír Církva
Institute of Chemical Process Fundamentals
Read the Original
This page is a summary of: Highly selective synthesis of [(perfluoroalkyl) methyl] oxiranes (by the addition of iodoperfluoroalkanes to allyl acetate), Journal of Fluorine Chemistry, July 1997, Elsevier,
DOI: 10.1016/s0022-1139(97)00018-3.
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