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Superelectrophilic activation of 1-nitronaphthalene in the presence of aluminum chloride. Reactions with benzene and cyclohexane

1-Nitronaphthalene smoothly reacts with benzene and undergoes selective reduction with cyclohexane in the presence of aluminum chloride to give 2,4,4-triphenyl-3,4-dihydronaphthalen-1(2H)-one oxime and 5,6,7,8-tetrahydro-1-naphthylamine, respectively. The mechanistic aspects of these and related rea...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-12, Vol.16 (47), p.9129-9132
Main Authors: Zhu, Zhongwei, Genaev, Alexander M, Salnikov, George E, Koltunov, Konstantin Yu
Format: Article
Language:English
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Summary:1-Nitronaphthalene smoothly reacts with benzene and undergoes selective reduction with cyclohexane in the presence of aluminum chloride to give 2,4,4-triphenyl-3,4-dihydronaphthalen-1(2H)-one oxime and 5,6,7,8-tetrahydro-1-naphthylamine, respectively. The mechanistic aspects of these and related reactions are discussed on the basis of DFT, providing insight into the protonation behavior of 1-nitronaphthalene coordinated to AlCl3.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02653j