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Synthesis 1987; 1987(6): 551-554
DOI: 10.1055/s-1987-27999
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Iodofluorination of Alkenes Using Bis(sym-collidine)iodine(I) Tetrafluoroborate

Robert D. Evans* , J. Herman Schauble
  • *Department of Chemistry, Villanova University, Villanova, PA 19085, U.S.A.
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Publication Date:
20 August 2002 (online)

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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.