Abstract
1,3-Dinitro[b, f][1,4]dibenzoxazepin-11(10H)-one enters nucleophilic substitution reactions with N-nucleophiles, azide ion preferably replacing the nitro group in position 3, whereas amines the one in position 1. Structures of the substitution products were confirmed by X-ray diffraction and 1H NMR NOE spectroscopy. The selectivity observed in the reaction with amines was supposed to be caused by the stabilization of the intermediate σ-complex with the NH…O intramolecular hydrogen bond.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2018–2022, October, 2007.
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Samet, A.V., Kislyi, K.A., Marshalkin, V.N. et al. Synthesis and structure of azido-and amino-substituted dibenzoxazepinones. Russ Chem Bull 56, 2089–2093 (2007). https://doi.org/10.1007/s11172-007-0325-4
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DOI: https://doi.org/10.1007/s11172-007-0325-4