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As generally known, the nitro group could exist in aliphatic nitrocopounds [1], nitroarenes [2], and as part of nitric (V) acid molecule [3-6]. Many years ago, Huisgen was establish [7], that -N(O)O moiety have nature of 1,3-dipole, similarly as azomethine ylides, imine oxides and many others, which easily react with unsaturated systems according to [2,3] cycloaddition scheme [7-10]. In consequence, above compounds may potential, attractive build blocks for synthesis of 1,3-dioxazole derivatives via [2,3]cycloaddition [8-10] with alkene/alkyne dipolarophiles. At this time no report on a product formed from [2,3]cycloaddition involving nitric (V) acid [11,12] but instead, there are many reports revealed about oxidation of graphenes, nanotubes, and fullerene family by using this acid [13,14]. There is a possibly that a meta-stable intermediate emerges between reactants and oxidation product. A literature review revealed that, the C-C double bond of the C20 fullerene is one of the most kinetically suitable unsaturated species for the reaction with 1,3-dipoles. According to the recent reports, the C20 fullerene could perform [2,3]cycloaddition reaction with dipolar species in a very fast process without needing any catalyst or accelerating agents [15,16]. Also a few reports revealed about adsorption of nitrogen dioxide on the surface of the C20 fullerene [17]. Therefore, the C20 fullerene was selected as an unsaturated species to be used in reaction with the nitro functional group (Scheme 1) to produce an intermediate which subsequently changes to an oxidation product.

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The Possibility of a Two-Step Oxidation of the Surface of C20 Fullerene by a Single Molecule of Nitric (V) Acid, Initiate by a Rare [2+3] Cycloaddition