Syntheses of α-Iodocarbonyl Compounds Using Bis(sym-collidine)Iodine(I) Tetrafluoroborate/Dimethyl Sulfoxide

Article abstract of DOI:10.1055/s-1986-31757

I(1+)(Collidine)2BF4(1-)/DMSO has been found to be a convenient reagent for the direct conversion of alkenes to α-iodocarbonyl compounds.Using conformationally biased alkenes, the reactions proceed stetreospecifically giving axial iodoketones.Application of the reagent in reactions with unsaturated carbohydrates provides a unique method for the conversion of certain glycals to their corresponding α-iodo-α,β-unsaturated lactones.