Abstract
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 π → π* 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.
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