67093-54-3Relevant academic research and scientific papers
Direct observation and kinetic characterization of o-quinodimethane and its radical cation variant generated in a photoinduced electron-transfer reaction of 1,2-bis(α-styryl)benzene
Ikeda, Hiroshi,Ikeda, Teruyo,Akagi, Megumi,Namai, Hayato,Miyashi, Tsutomu,Takahashi, Yasutake,Kamata, Masaki
, p. 1831 - 1835 (2005)
Nanosecond time-resolved absorption spectroscopy on the laser flash photolysis of 1,2-bis(α-styryl)benzene (1) under N-methylquinolinium tetrafluoroborate-toluene-sensitized conditions in acetonitrile confirmed that an o-quinodimethane radical cation (2+, λmax = 569 nm) decayed and the corresponding neutral prototype (2, λmax = 444 nm) rose with rate constants of 5.6 and 5.9 × 105 s -1, respectively, showing the first agreement in kinetics between a reactive radical cation intermediate intervening in chemical reaction and the corresponding neutral species formed by back electron transfer.
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.
Acid-catalyzed rearrangement of cyclobutanols. Syntheses of chrysenes, cyclopentenophenanthrenes, and diarylmethanes
Lee-Ruff, Edward,Hopkinson, Alan C.,Kazarians-Moghaddam, Hira,Gupta, Brij,Katz, Morris
, p. 154 - 159 (2007/10/02)
Acid-catalyzed reactions of 8-aryl or 8,8-diarylbicyclooct-2-en-7-ols lead to tetrahydrophenanthrene derivatives.For example 8-(1-naphthyl)-bicyclooct-2-en-7-ols give substituted chrysenes in methanesulphonic acid.In the case of the homologous 7-aryl or 7,7-diarylbicyclohept-2-en-6-ols a novel transformation of diarylmethanes is observed.A mechanism is proposed which accounts for the product distribution observed in these rearrangements.
