Issue 7, 1989

Conformations of derivatives of 3,7-diazabicyclo[3.3.1]nonan-9-one. Comparison of 3-ethoxycarbonyl-7-methyl-1,5-diphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one and 3,7-di(ethoxycarbonyl)-1,5-diphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one: effect of a nucleophile ⋯ electrophile interaction on molecular geometry

Abstract

X-Ray analyses of 3-ethoxycarbonyl-7-methyl-1,5-diphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one (4) and 3,7-di(ethoxycarbonyl)-1,5-diphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one (5) have established that both molecules adopt twin-chair conformations. In compound (5) the urethane N atoms have the expected nearly coplanar arrangement of bonds whereas in compound (4) the urethane N atom has a distinctly pyramidal pattern of bonds; the N–CO2Et bond in (4) is bent out of the CH2–N–CH2 plane towards the NMe group so that the N ⋯ C separation between the NMe and CO2Et groups is 2.665 Å whereas the corresponding distances in compound (5) are 3.363 and 3.150 Å. The results demonstrate the existence of an attractive nucleophile–electrophile interaction in (4).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1989, 831-834

Conformations of derivatives of 3,7-diazabicyclo[3.3.1]nonan-9-one. Comparison of 3-ethoxycarbonyl-7-methyl-1,5-diphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one and 3,7-di(ethoxycarbonyl)-1,5-diphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one: effect of a nucleophile ⋯ electrophile interaction on molecular geometry

P. H. McCabe, N. J. Milne and G. A. Sim, J. Chem. Soc., Perkin Trans. 2, 1989, 831 DOI: 10.1039/P29890000831

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