Year 2007, Month 10 (Section Full Articles, Page 2089)
Synthesis and structure of azido- and amino-substituted dibenzoxazepinones
A. V. Samet, K. A. Kislyi, V. N. Marshalkin, Yu. A. Strelenko, Yu. V. Nelyubina, K. A. Lyssenko, and V. V. Semenov
1,3-Dinitro[b, f ][1,4]dibenzîxazepin-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 1Í 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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