Highly selective synthesis of [(perfluoroalkyl)methyl]oxiranes (by the addition of iodoperfluoroalkanes to allyl acetate)

Article abstract of DOI:10.1016/S0022-1139(97)00018-3

Mixtures of regioisomeric adducts of monoiodoperfluoroalkanes R_F-I (R_F = C₄F₉, C₆F₁₃, C₈F₁₇) with allyl acetate, R_FCH₂CHICH₂OAc (1a-1c) and rearranged adducts R_FCH₂CH(OAc)-CH₂I (2a-2c), were converted chemoselectively to the corresponding oxiranes R_FCH₂CH(-O-)CH₂ (3a-3c) in yields of 94-96% (total yields of the two-step synthesis starting from R_F-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 R_FCH=CHCH₂OAc (4a-4c) and R_FCH=CHCH₂OH (5a-5c) in the epoxidation reaction was studied.