Abstract
N-(Nitramino)phthalimide R2N-NHNO2 (R2NH is phthalimide) was synthesized by nitration of N-aminophthalimide with nitronium tetrafluoroborate. The structure of this compound was established by X-ray diffraction and confirmed by 1H, 13C, and 14N NMR spectroscopy. The methylation of this compound with diazomethane affords a mixture of N-methyl (R2N-NMeNO2) and O-methyl (R2N-N=N(O)OMe) isomers. The latter compound contains the previously unknown high-nitrogen-oxygen fragment. The thermal decomposition of N-(nitramino)phthalimide in vacuo at 80–100 °C gives 2H-3,1-benzoxazine-2,4(1H)-dione (isatoic anhydride) as the major product.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 625–630, March, 2008.
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Klenov, M.S., Churakov, A.M., Anikin, O.V. et al. Synthesis, structure, and properties of N-(nitramino)phthalimide. Russ Chem Bull 57, 638–643 (2008). https://doi.org/10.1007/s11172-008-0100-1
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DOI: https://doi.org/10.1007/s11172-008-0100-1