1995 ring closure reactions ring closure reactions O 0130
-055Reaction of peri-Acyloxynaphthyl α-Bromomethyl Ketones with Oand N-Containing Nucleophiles.-Reaction of the title ketones (I) with aliphatic amines and pyridine results in formation of cyclized products (II) and (III), resp., whilst reaction of (I) with aromatic amines and AcONa provides substitution products (cf. (V), (VII)). -(MINYAEVA, L. G.; GOLYANSKAYA, O. M.; MEZHERITSKII, V. V.; Zh. Org. Khim. 30 (1994) 2, 258-260; Tul. gos. pedagog. inst. im. Tolstogo, Tula, Russia; RU)
Spectral and quantum-chemical investigation of ortho-and peri-hydroxy-substituted aldehydes, 1,5-naphthalenediol derivatives, was carried out. An unusual spin-spin coupling through an intramolecular hydrogen bond was discovered in the molecule of 1,5-dihydroxynaphthalene-4,8-dicarbaldehyde. It was shown that this dialdehyde is involved into the ring-chain tautomerism. The position of this equilibrium was examined depending on the temperature and the solvent polarity. The effect of the solvent polarity on the benzoid-quinoid tautomerism in the dihydroxynaphthalene-2,6-dicarbaldehyde was established. By the method of quantum-chemical calculations the relative energy stability and conformational structure of dialdehydes were revealed.
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