103224-73-3Relevant 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 (1987)
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.
Regioselective Side-Chain Nitration of Polymethylbenzenes Directed by an Acyl Function and Its Application to the Synthesis of Polysubstituted Phthalic Acid Derivatives
Keumi, Takashi,Morita, Toshio,Teramoto, Koichi,Takahashi, Hisakazu,Yamamoto, Hiroshi,et al.
, p. 3439 - 3446 (2007/10/02)
Nitration of three types of tetramethylacetophenones and pentamethylacetophenone with fuming nitric acid in acetic anhydride was carried out.The product distributions were compared with those estimated from substituent effects.A variety of acylpentamethylbenzenes including pentamethylbenzoic acid were reacted with the nitrating system to give regioselectively 2-(nitromethyl)-3,4,5,6-tetramethylacylbenzenes.The selective nitrations of some benzoic acid derivatives followed by an alkaline treatment have been found to provide the N-hydroxyphthalimide derivatives, which a re readily converted to the phthalic anhydrides and the phthalazines.
