The effect of meta-substituents in the aromatic ring on the route of C
laisen rearrangement of N-(pent-3-en-2-yl)-3-fluoro(or 3-trifluorometh
yl, 3,4-difluoro)anilines induced by ZnCl2 was investigated. The forma
tion of two possible ortho-alkenylated reaction products was observed.
The ratio of these isomers depends on the nature of the acid catalyst
.