ChemInform Abstract: Preparation of Perfluoroalkyl Azaarenes with a Perfluoroalkyllithium- Boron Trifluoride System.

Abstract

Abstract In the presence of boron trifluoride, perfluoroalkyllithiums generated in situ from tbe reaction of n-perfluoroalkyl iodides with methyllithium-lithium bromide smoothly added to a carbon-nitrogen double bond of bicyclic azaarenes and diazines to give the corresponding perfluoroalkylated dihydro heterocycles, which often underwent spontaneous aromatization in air. Perfluoroalkylation occurred preferentially at the carbon next to nitrogen in azaarenes even when the carbon atom was occupied by an alkyl substituent. Only one exception observed was the reaction of acridine where a perfluoroalkyl group was introduced at 9 position.