Conversion of aldoximes to nitriles with trifluoracetic anhydride and sodium carbonate

CHED 368

Justin C. Hadar, r-kjonaas@indstate.edu and Richard A. Kjonaas, r-kjonaas@indstate.edu. Department of Chemistry, Indiana State University, Terre Haute, IN 47809
In our attempt to oxidize aldoximes to nitro compounds with trifluoroperoxyacetic acid prepared from trifluoroacetic anhydride and sodium percarbonate, we noticed that the aldoximes were cleanly converted to nitriles. This simple dehydration, however, should not require an oxidizing agent so we replaced sodium percarbonate with sodium carbonate and obtained the same results. Further experiments showed that this trifluoroacetic anhydride/sodium carbonate method complements the wide variety of other aldoxime-to-nitrile dehydration procedures.