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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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Published in: | Organic & biomolecular chemistry 2018-12, Vol.16 (47), p.9129-9132 |
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Main Authors: | , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/c8ob02653j |