Issue 47, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
26 oct. 2018
Accepted
14 nov. 2018
First published
21 nov. 2018

Org. Biomol. Chem., 2018,16, 9129-9132

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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