Synthesis and chiral-optical properties of some benzolactams

Five- and seven-membered benzolactarns — (–)-S-2, 3-dimethyl-2, 3-dihydroisoindolone and (+)-S-5-methyl-2, 3, 4, 5-tetrahydrobenz[c]azepin-1-one — were synthesized. A study of their chiral-optical properties and comparison with the previously studied six-membered lactam (–)-S-4-methyl-3, 4-dihydroisoquinol-1-one showed that their circular dichroism spectra are similar: The spectra contain dichroic absorption bands due to ^* transitions in the aromatic chromophore (270 and 220 nm) and a band of charge transfer in the benzamide chromophore at 240–250 nm. The magnitude of the Cotton effect due to the charge-transfer band increases as the lactam ring becomes larger (five-membered < six-membered < sevenmembered benzolactam). The change in the magnitude of the Cotton effect is explained by the development of a strictly dissymetric chromophore.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 656–662, May, 1978.