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Issue 10, 1993
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Conformation of 6-morpholino-3-azabicyclo[3.1.0]hexane derivatives


1 H NMR spectroscopic studies established the presence of a chair conformation for endo-3-methyl-6-morpholino-3-azabicyclo[3.1.0]hexane derivatives 8a and b. This was additionally confirmed by an X-ray structural analysis of 8b. The diastereomers 10a,b and the N-demethyl-endo-morpholino compounds 9a,b, however, were found to prefer a boat conformation. The correlation between dihedral angles and ring buckle of 3-azabicyclo[3.1.0]hexane 4 was determined by MNDOC semiempirical calculations. Further structural information about this bicyclic system was obtained by HF/6–31 G* calculations for the 3-azabicyclo[3.1.0]hexane parent compounds 4 and 5.

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Article information

J. Chem. Soc., Perkin Trans. 2, 1993, 1901-1905
Article type

Conformation of 6-morpholino-3-azabicyclo[3.1.0]hexane derivatives

C. Tetzlaff, V. Butz, E. Vilsmaier, R. Wagemann, G. Maas, A. R. von Onciul and T. Clark, J. Chem. Soc., Perkin Trans. 2, 1993, 1901
DOI: 10.1039/P29930001901

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