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Issue 47, 2018
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Superelectrophilic activation of 1-nitronaphthalene in the presence of aluminum chloride. Reactions with benzene and cyclohexane

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Abstract

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.

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

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Article information


Submitted
26 Oct 2018
Accepted
14 Nov 2018
First published
21 Nov 2018

Org. Biomol. Chem., 2018,16, 9129-9132
Article type
Communication

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

Z. Zhu, A. M. Genaev, G. E. Salnikov and K. Yu. Koltunov, Org. Biomol. Chem., 2018, 16, 9129
DOI: 10.1039/C8OB02653J

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