2-Aza-A-homo-5α-cholestan-1-one (2), which exhibits and n→π* c.d. Cotton effect with the sign opposite to that predicted by Ogura's sign rule, is shown by X-ray diffraction to contain a quasi-chair seven-membered lactam ring with a mean C-7–NH–CO–C-3 dihedral angle of –20° indicating that the ‘amide’ chromophore is twisted in a way which is opposite to that of caprolactam (1).
H. Suginome and A. Furusaki, J. Chem. Soc., Chem. Commun., 1979, 782 DOI: 10.1039/C39790000782
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