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Nitroxide Chemistry. Part 13. Reaction of NN-Bis(trifluoromethyl)amino-oxyl with Hexafluoroisopropylideneimine and Related Compounds
Fisher, Raymond,Haszeldine, Robert N.,Tipping, Anthony E.
, p. 406 - 409 (2007/10/02)
The initial product from reaction of the oxyl (CF3)2N-O. with hexafluoroisopropylideneimine is the substituted imine (CF3)2C=N-O-N(CF3)2 (isolated in 81percent yield) which, via further oxyl attack at carbon, gives the compounds (CF3)2CO, (CF3)2N-NO, (CF3)2N-O-N(CF3)2, and (CF3)2N-O-C(CF3)2N+(O-)=N-C(CF3)2-O-N(CF3)2.Oxyl attack on hexafluoroacetone oxime affords as major products (CF3)2CO, (CF3)2NH, and (CF3)2N-O-NO.The oxyl reacts with hexafluoroacetone anil to yield a hexaoxyl adduct, with hexafluoroacetone hydrazone to afford the diazoalkane (CF3)2CN2 (100percent), and with hexafluoroacetone azine to give the bis-1:4-adduct (CF3)2N-O-C(CF3)2-N=N-C(CF3)2-O-N(CF3)2 (100percent).Thus, initial radical attack of the oxyl invariably takes place at carbon in the series of imines studied.
