Abstract
A series of previously undescribed 3-(1-hydroxy-4-methyl-2-naphthyl)propenal imines was synthesized. In the crystalline state all of the imines, except the N-(p-nitrophenyl)imine, have an open o-quinoid structure, whereas in solutions in nonpolar solvents they exist in the cyclic 2H-chromene form. In polar solvents the imines display ring-chain tautomeric equilibrium of the 2H-chromene and o-quinoid forms, the relative percentages of which are determined by the character of the substituent in the amino component of the molecule and by the polarity of the solvent. The N-(p-nitrophenyl)imine has-the 2H-chromene structure in the solid phase and in solvents.
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Communication 14 from the series “Photochromic and thermochromic spirans.” See [1] for communication 13.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1031–1039, August, 1983.
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Andreeva, I.M., Babeshko, O.M., Bondarenko, E.M. et al. Ring-chain tautomerism and thermo- and photochromism of 3-(1-hydroxy-4-methyl-2-naphthyl)propenal imines. Chem Heterocycl Compd 19, 824–831 (1983). https://doi.org/10.1007/BF00516440
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DOI: https://doi.org/10.1007/BF00516440