Synthesis, structure, and properties of N-(nitramino)phthalimide

Synthesis, structure, and properties of N-(nitramino)phthalimide Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2008, Volume: 57, Number: 3, Pages: 638-643 Pages count : 6 DOI: 10.1007/s11172-008-0100-1

Authors

Klenov M.S. ¹ , Churakov A.M. ¹ , Anikin O.V. ¹ , Strelenko Yu.A. ¹ , Fedyanin I.V. ² , Lyssenko K.A. ² , Tartakovsky V.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

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.

Klenov M.S. , Churakov A.M. , Anikin O.V. , Strelenko Y.A. , Fedyanin I.V. , Lyssenko K.A. , Tartakovsky V.A.
Synthesis, structure, and properties of N-(nitramino)phthalimide
Russian Chemical Bulletin. 2008. V.57. N3. P.638-643. DOI: 10.1007/s11172-008-0100-1 WOS Scopus OpenAlex

≡ Web of science:	WOS:000263566900030
≡ Scopus:	2-s2.0-62249195489
≡ OpenAlex:	W2118569829