Abstract
Abstract An annelated[14]annulenedione (V) was prepared by the Castro reaction of cuprous salt of o-iodocinnamoylacetylene (IV) in order to examine the aromatic character of the inner fourteen membered ring. The NMR spectra of V in arsenic trichloride and deuterotrifluoroacetic acid suggest that significant downfield shift of the inner protons HB is due to a paramagnetic ring current arising from polarization of two carbonyl groups in the inner ring, compared with the spectra of a reference compound VI.
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