Iodofluorination of Alkenes Using Bis(sym-collidine)iodine(I) Tetrafluoroborate

Abstract
I+(Collidine)2BF4 - in dichloromethane has been found to be a convenient reagent for regio- and stereospecific conversion of a variety of cycloalkenes to vicinal trans-iodofluorocycloalkanes. With bicyclo[2.2.1]heptene and bicyclo[2.2.1]heptadiene, only tricyclic products were obtained. Application of the title reagent to certain glycal esters provides a new method for stereoselective synthesis of trans-diaxial iodopyranosyl fluorides.

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