Cascade reaction of 2,3-naphthalenediol with benzene in the presence of aluminum halides |
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| Authors: | Zhongwei Zhu George E Salnikov Konstantin Yu Koltunov |
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| Institution: | 1. Novosibirsk State University, Novosibirsk 630090, Russian Federation;2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090, Russian Federation;3. International Tomography Center, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090, Russian Federation;4. G. K. Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090, Russian Federation |
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| Abstract: | 2,3-Naphthalenediol on superelectrophilic activation with aluminium halides smoothly reacts with benzene to give 4-((3-phenyl-1H-inden-1-yl)methyl)benzene-1,2-diol, which in turn undergoes intramolecular cyclization to form 5,10-methano-5-phenyldibenzoa,d]cycloheptane-2,3-diol. The mechanistic aspects of these unusual transformations are discussed. |
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| Keywords: | Naphthols Superelectrophilic activation Electrophilic aromatic substitution Ionic reduction |
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