Fluorination of norbornadiene and 1,4-dihydro-1,4-methanonaphthalene with substituted (difluoroiodo)benzenes

Abstract

The reaction of substituted (difluoroiodo)benzenes with norbornadiene results in four products: 3-exo,5-endo-(2)(49–55%), 3-exo,5-exo-(3)(15–20%), and 3-endo,5-endo-difluorotricyclo[2.2.1.0]heptane (4)(6–8%), and 5-exo,7-syn-difluoronorborn-2-ene (5)(18–32%), depending upon the substituent in the benzene ring. The reaction with 1,4-dihydro-1,4-methanonaphthalene results in 2-exo,9-syn-difluoro-1,4-dihydro-1,4-methanonaphthalene.