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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Synthesis of dixanthones and poly(dixanthone)s by cyclization of 2-aryloxybenzonitriles in trifluoromethanesulfonic acid.

[reaction: see text] Condensation of 2-fluorobenzonitriles with phenoxides affords 2-aryloxybenzonitriles that cyclize cleanly in trifluoromethanesulfonic acid at room temperature to give xanthone-iminium triflates. The C=N bond in these compounds is remarkably resistant to hydrolysis, but prolonged reaction with strong aqueous acid under vigorous conditions affords xanthones in good yield. The synthesis is exemplified for a novel series of polynuclear dixanthones and for a high molar mass polyxanthone derived from the previously unreported monomer 3,3'-difluoro-4,4'-biphenyldicarbonitrile.[1]

References

  1. Synthesis of dixanthones and poly(dixanthone)s by cyclization of 2-aryloxybenzonitriles in trifluoromethanesulfonic acid. Colquhoun, H.M., Lewis, D.F., Williams, D.J. Org. Lett. (2001) [Pubmed]
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