Abstract
1-Cyano-1-methylethyl radicals produced by the decomposition of α, α'-azobisisobutyronitrileattacked the nitro group of nitrobenzene, m-dinitrobenzene andtetranitromethane yielding hydrogen cyanide, acetone and, in the case of thefirst two compounds, N-phenyl-and N-(m-nitrophenyl)-O, N-bis-(1-cyano-1-methylethyl) hydroxylamines. Nitromethane and ethyl nitrate did not react withthis radical. There was a rough parallelism between the amount of acetoneproduced in the present reaction and the retarder efficiency of nitro compoundsin the polymerization. Thus, it is concluded that retardation of the viny polymerizationby aromatic nitro compounds is due to formation of polymer alkoxyradicals and a nitroso compound by reaction of the nitro group with growingpolymer radicals. The nitroso compound thus formed combines with two growingpolymer radicals to yield a trisubstituted hydroxylamine.
