Oxidative nitration reaction of antiaromatic 5,15-dioxaporphyrin

Upon oxidation of 20[Formula: see text]-electron antiaromatic 5,15-dioxaporphyrin (DOP) using nitrosonium ions as oxidants, a tetrakis-[Formula: see text]-nitrated compound was formed instead of the expected 18[Formula: see text]-electron aromatic dication species via an oxidative nitration reaction mechanism. Compared with the original DOP, this tetranitro DOP product exhibited a blue shift of absorption and downfield shifts of the [Formula: see text]-pyrrolic proton signals. The unique antiaromatic electronic structure of the tetranitro DOP was disclosed experimentally by electrochemistry and theoretically by DFT and NICS calculations.

5-(Dinitromethyl)-3-(trinitromethyl)-1,2,4-triazole and its derivatives: a new application of oxidative nitration towards gem-trinitro-based energetic materials

A family of 5-(dinitromethyl)-3-(trinitromethyl)-1,2,4-triazole and its derivatives was prepared using a new application of oxidative nitration with gem-trinitro-based energetics. These new compounds show promise for future energetic materials.

Direct oxidative nitration of aromatic sulfonamides under mild conditions

This efficient reaction proceeds under very mild conditions with low cost nitration reagents and can be applied in gram-scale preparation.