111895-18-2Relevant academic research and scientific papers
An Interpretation of the Puzzling Dichotomy of the Reaction Modes Observed during the Side-chain Nitration of Alkylaromatics
Suzuki, Hitomi,Koide, Hideki,Taki, Yukiko,Ohbayashi, Eiichi,Ogawa, Takuji
, p. 891 - 894 (2007/10/02)
Nitration of substituted pentamethylbenzenes has been carried out under various conditions using the title nitrating systems in order to elucidate the peculiar dependence of the modes of side-chain substitution on the reagent employed; nitrooxylation with HNO3/CH2Cl2 and nitration with HNO3/(CH3CO)2O.Based on the evidence obtained from product variations with substituents, electrochemical nitrodecarboxylation of arylacetates, and ESR examination of the initial stage of the side-chain reactions, a proposal is made that the side-chain substitution of polysubstituted arenes occurs via a heterolytic path with HNO3/CH2Cl2 and via a homolytic path with HNO3/(CH3CO)2O.
