Triflamidation of Camphene in Nitrile Medium

The reactions of triflamide with camphene in nitriles in the presence of N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) have been studied. The reactions in isobutyronitrile led to the formation of a number of products, including dibromide, camphenol, bromoamidation product, and the corresponding amidines. Two isomeric benzamidines were obtained in benzonitrile in the presence of NBS. One of these was the skeletal rearrangement product, and the other retained the initial structure. The reaction of camphene with NIS in benzonitrile produced a similar mixture of isomers containing iodine instead of bromine.