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Methano-Bridged 14?-Electron Aromatic Annulenes. 2. 5-Methoxy-7,12-methano-6-azabenzannulene and the Benzenesulfonate Ester of 5-Hydroxy-7,12-methano-6-azabenzannulene
Hunadi, Ronald J.,Helmkamp, George K.
, p. 2880 - 2884 (1981)
The syntheses of 5-methoxy-7,12-methano-6-azabenzannulene (4) and the benzenesulfonate ester of 5-hydroxy-7,12-methano-6-azabenzannulene (5) are described.Compounds 4 and 5 were shown to be delocalized aromatic systems as evidenced by their 13C and 1H NMR chemical shifts.Ester 5 was prepared by Beckmann rearrangement of 7a (which was available from anion 6 by treatment with tert-butyl nitrite).Hydrolysis of 5 with potassium hydroxide followed by alkylation with trimethyloxonium tetrafluoroborate gave the benzannulene 4.
