Reactions involving fluoride ion. Part 36. Aromatic amines as carbon nucleophiles in reactions with unsaturated fluorocarbons

Abstract

N,N-Dimethylaniline and N-methylindole react as carbon nucleophiles with perfluorocycloalkene derivatives, giving products 6a and 6b arising from allylic displacement. 1,8-Bis(dimethylamino)naphthalene 7, reacts through the 4,5-positions as a difunctional nucleophile, giving a novel annelation. Reactions with 2 and 3 are regiospecific leading to products 9 and 8, respectively. Reaction of perfluorobicyclopentylidene 4 with 7 gives first, through defluorination, the diene 19 and then by annelation of this the product 14. The colours of the products are evidence of extensive charge separation.