THE BECKMANN REARRANGEMENT OF FLUOROKETOXIMES

In phosphorous pentaohloride-ohloroform, a, a, a-trifluoroaoetophenone oxime (1), a, , a-trifluoro-p-methylacetophenone oxime (2), a, a, a-trifluoro-pmethoxyaoetophenone oxime 3), henyl heptafluoropropyl ketoxime (4) and oyolohexyl trifluoromethyl ketoxime (5) could undergo eokmann rearrangement,and they all rearranged to the corresponding N-substituted perfluoro cid mides. In polyphosphoric aoid, only 1, 2, and 5 could give Beokmann rearrangement products, 3 as carbonized, 4 gave no reaotion and the starting oxime was recovered. When these fluoro etoximes were treated with benzenesulfonyl ohloride in pyridino, they gave no rearranged roducts, only the corresponding benzenesulfonates of 1, 2, 3, 4 and 5 were obtained.