Masked acylation of m-Dinitrobenzene and deriviatives with nitroalkanes under basic conditions: Nitromethylation and α-(hydroxyimino)alkylation

Article abstract of DOI:10.1016/S0040-4039(98)02552-0

m-Dinitrobenzene and derivatives react with nitromethane or some other primary nitroalkanes in the presence of lithium tert-butoxide in 1,3- dimethyl-2-imidazolizinone (DMI) at room temperature, giving the corresponding 4-nitromethyl and 4-[1-(hydroxyimino)alkyl] derivatives, respectively, in moderate yields. These products are smoothly converted to the corresponding carbonyl compounds by oxidative Nef reaction using ozonized oxygen.