Journal of Organic Chemistry p. 2880 - 2884 (1981)
Update date:2022-08-05
Topics:
Hunadi, Ronald J.
Helmkamp, George K.
The syntheses of 5-methoxy-7,12-methano-6-azabenz<10>annulene (4) and the benzenesulfonate ester of 5-hydroxy-7,12-methano-6-azabenz<10>annulene (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 benz<10>annulene 4.
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Doi:10.1039/P19810000105
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(1981)
