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- W2066923009 abstract "The titled annulenone 6, the first benz-annelated 11-membered fully conjugated ketone, has been prepared by the aldol type condensation of 3-benzoxepin-2,4-dialdehyde 3 and dimethyl acetone-dicarboxylate. Some evidence for the nonaromatic character of 6 could be obtained from the NMR and IR spectra as well as protonation behaviour of 6. The NMR spectrum of 6 in conc H2SO4 confirmed the presence of an aromatic 1-hydroxy-6,7-benzo-4,9-oxido[11]annulenyl cation 7. 6,7-Benzo-4,9-oxido-1-hydroxy-1-homo[10]annulene 11 was prepared by the NaBH4 reduction of 6. The treatment of 11 with CF3COOH regenerated another completely delocalized [11]annulenyl cation 12. The pkR+ of 12 was obtained as −4·1, spectrophotometrically. The electronic spectra of these novel cations (7 and 12) were found to be similar to those of 4,5-(2′,3′-naphtho)tropylium cations (13a and 13b), respectively." @default.
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- W2066923009 date "1973-01-01" @default.
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- W2066923009 title "The synthesis of 6,7-benzo-4,9-oxido[11]annulenone and aromatic 6,7-benzo-4,9-oxido[11]annulenyl cations" @default.
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- W2066923009 doi "https://doi.org/10.1016/0040-4020(73)80005-5" @default.
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