NN′-dialkoxy-NN′-bis(trifluoromethyl)hydrazines, novel products from the reaction of alkoxyl radicals with trifluoronitrosomethane

Alkoxyl radicals, generated by nitrite photolysis, react with trifluoronitrosomethane to yield NN′-dialkoxy-NN′-bis-(trifluoromethyl)hydrazines. An 18O-labelling experiment indicated complete retention of the alkoxy-oxygen atom. When the products are heated with thioglycolic acid, cracking leads to the hydroxylamines, RO·NH·CF3. For the case where R is 1-adamantyl, further stepwise conversion into O-(1-adamantyl)hydroxylamine has been achieved.