Alkanes nitroxylation

Bis(trifluoromethyl)nitroxyl readily attacks the C = C bond of fluoroalkenes. Two radicals add across the C = C bond95-97 to give the corresponding vicinal bis[bis(trifluoromethyl)amino-oxy]alkanes 60 in 80% to quantitative yields. Even fluoroaromatic compounds react in the same way (vide infra). 

The oxidation of primary and secondary alcohols by stable organic nitroxyl radicals has been reviewed.111 The kinetics of reactions of alkanes and arenes with peroxynitrous acid suggest the participation of the same active oxidizing species in both gas and aqueous phase HOONO or its decomposition product OONO. 112 The oxidation of the alkaloids reserpine and rescinnamine by nitric acid has been studied.113... 

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