Nitroxide chemistry. Part 13. Reaction of NN-bis(trifluoromethyl)amino-oxyl with hexafluoroisopropylideneimine and related compounds
Abstract
The initial product from reaction of the oxyl (CF3)2N–O˙ with hexafluoroisopropylideneimine is the substituted imine (CF3)2C![[double bond, length half m-dash]](https://www.rsc.org/images/entities/char_e006.gif)
N–O–N(CF3)2(isolated in 81% 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)2[graphic omitted]([graphic omitted])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(100%), and with hexafluoroacetone azine to give the bis-1 : 4-adduct (CF3)2N–O–C(CF3)2–NN–C(CF3)2–O–N(CF3)2(100%). Thus, initial radical attack of the oxyl invariably takes place at carbon in the series of imines studied.
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