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Issue 12, 2002
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Conformational NMR study of N-substituted-1,3,4,5-tetrahydro-1H-2-benzazepines

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Abstract

The variable temperature (298–179 K) 1H NMR spectra of N-substituted 2-benzazepines (compounds 27) correspond to two puckered mirror-image (enantiomorphic) conformations, with a single chair-to-chair interconversion barrier for the benzazepine ring of ca. 11 kcal mol−1 in CD2Cl2 solution. A similar interconversion was detected for 1,3,4,5-tetrahydro-N-methylbenzazepine (compound 1), of lower symmetry. The conformations of compounds 17 were assigned on the basis of the magnitude of 1H-1H vicinal coupling constants. The 1H and 13C NMR spectral assignments were determined by 1H–1H COSY, 1H–13C COSY, and NOESY experiments.

Graphical abstract: Conformational NMR study of N-substituted-1,3,4,5-tetrahydro-1H-2-benzazepines

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Publication details

The article was received on 06 Sep 2002, accepted on 17 Oct 2002 and first published on 22 Nov 2002


Article type: Paper
DOI: 10.1039/B208633F
Citation: J. Chem. Soc., Perkin Trans. 2, 2002,0, 1986-1993
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    Conformational NMR study of N-substituted-1,3,4,5-tetrahydro-1H-2-benzazepines

    A. R. Katritzky, N. G. Akhmedov, I. Ghiviriga and R. Maimait, J. Chem. Soc., Perkin Trans. 2, 2002, 0, 1986
    DOI: 10.1039/B208633F

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