67093-48-5Relevant academic research and scientific papers
REACTION OF PHENOLS AND THEIR DERIVATIVES WITH AROMATIC COMPOUNDS IN THE PRESENCE OF ACIDIC AGENTS. XIII. REACTION OF DERIVATIVES OF 2-NAPHTHOL WITH BENZENE. REGIOSELECTIVITY AND REACTION MECHANISM
Koltunov, K. Yu.,Repinskaya, I. B.,Shakirov, M. M.,Shchegoleva, L. N.
, p. 88 - 96 (2007/10/02)
1-Methyl and 1-phenyl-2-naphthols react with benzene in the presence of aluminum chloride with the formation of 1-methyl-4-phenyl- and 1,4-diphenyl-2-tetralones respectively. 1,3-Naphthalenediol and its dimethyl ether enter into an analogous reaction in the presence of aluminum chloride or in the HF-SbF5 system with the formation of 3-phenyl-1-naphthol and its methyl ether respectively.It was concluded that the regioselectivity and other features of the condensations are due to the reactivity of the key intermediates of the reaction, i.e., the diprotonated forms of the 2-naphthols (dications) or, for the analogs in the presence of aluminum halides, the mono-C-protonated complexes of the tautomeric keto forms of naphthols with the aluminum halides.The latter agrees with the results from MNDO quantum-chemical calculations for the dications.
