Conformational Analysis About N–N Bond by NMR Spectroscopy: N-Sulphonyl Derivatives of N-Aminoimides of Anthracene-Citraconic Anhydride and Naphthalene-Maleic Anhydride Adducts

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A series of N′,N′-disulphonyl and N′-sulphonyl-N′-acetyl derivatives of N-amino-9,10-dihydroanthracene-9,10-endo-α-methyl-α,β-succinimide and N-amino-1,2,3,4-tetrahydro-1,4-etheno/ethano-naphthalene-2,3-exo/endo-dicarboximides with a benzo ring in the cage-moiety were prepared and their NMR spectra were studied. Shielding constants of the substituents provide evidence for the non-eclipsed conformations of the N′-substituents with the ring carbonyls. The preferred conformations of N′-sulphonyl-N′-acetyl derivatives are explained on steric grounds. In N′-tosyl-N′-acetyl derivatives the tosyl group takes up a fixed conformation about N′-SO2 bond in which the aryl part of the tosyl group projects away from the cage-moiety.
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