NOVEL TRANSFORMATIONS WITH BORONTRIFLUORIDE ETHERATE/IODIDE ION : FACILE CONVERSION OF 2-KETOOXIRANES AND 2-BROMO-2-ENONES TO THE α,β-UNSATURATED CARBONYL COMPOUNDS.

Article abstract of DOI:10.1016/S0040-4020(01)81738-5

Borontrifluoride etherate/iodide ion rapidly deoxygenates α-ketooxiranes, 3, to the corresponding α,β-unsaturated carbonyl compounds, 4, in near quantitative yields.In contrast, the reaction of 3 with borontrifluoride etherate/bromide ion, 2, yielded the corresponding 2-bromo-2-enone derivatives, 5, in excellent yields.The reagent 1, also dehalogenates a variety of 2-bromo-2-enones, 5, to the corresponding 2-en-1-one derivatives, 4, in high yields.