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The tropone-fused 1,6-methano[10]annulene 4 was synthesized from 3,4-bis(bromomethyl)-1,6-methano[10]annulene and the protonation of 4 provided the hydroxytropylium ion-fused annulene 5. 1 H NMR spectra of 4 and 5 exhibited an unequal shielding effect on the bridge hydrogens from the resulted π ring system, suggesting the existence of the significant homoconjugative transannular interaction...
New thiophene-annulated 1,6-methano[10]annulene 1 and 2 were synthesized. The anisotropic deshielding effect from the π-electron system, based on the chemical shift values of the bridged methylene protons, is reduced compared with that of 3, and their crystal structures show clear bond alternation.
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