Tetrahedron p. 4619 - 4626 (1995)
Update date:2022-08-11
Topics:
Alarcon, Sergio H.
Olivieri, Alejandro C.
Labadie, Guillermo R.
Cravero, Raquel M.
Gonzalez-Sierra, Manuel
The synthesis of 10-hydroxyphenanthrene-9-carbaldehyde and its anil are described.The structure of the latter compound has been thoroughly studied by 1H and 13C NMR, UV-visible absorption, fluorescence and IR spectroscopies.All the experimental results support the existence of this anil mainly in the keto-enamine tautomeric form.A comparison is presented with previously studied anils derived from salicylaldehyde and 2-hydroxynaphthalene-1-carbaldehyde.Semiempirical calculations (AM1) concerning the relative stability of tautomers as well as the optimized molecular geometries are in good agreement with the experimental findings.
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