Synthesis and Properties of Dinitromethylated Arenes. Reinvestigation of the Ponzio Reaction

Article abstract of DOI:10.1246/bcsj.61.2927

Several title compounds have been prepared by the modified Ponzio procedure and their IR, 1 H and 13 C NMR data are presented.In some cases trinitromethylated arenes were obtained as a by-product.Oxidative cleavage to parent aldehydes and oxidation to carboxylic acids were the major competing reactions. 9-Anthracenecarbaldehyde oxime and 10-methyl-9-anthracenecarbaldehyde oxime reacted with nitrogen dioxide in an unexpected way, giving 10-nitro-9-anthracenecarbonitrile oxide and 10-methyl-10-nitro-9-anthrone as the respective main products.Nitration of (dinitromethyl)benzene has also been examined under various conditions.