Transformation of Dialkyl-Substituted Alkynes under the Action of the TaCl<sub>5</sub>-Mg and NbCl<sub>5</sub>-Mg Reagent System
A regioselective method for the preparation of <i>p</i>-tolyl-substituted alkanes is presented based on the reaction of dialkyl-substituted alkynes with four equivalents of TaCl<sub>5</sub> or NbCl<sub>5</sub> in the presence of stoichiometric amounts of metallic...
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MDPI AG
2021-11-01
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| Series: | Chemistry Proceedings |
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| Online Access: | https://www.mdpi.com/2673-4583/8/1/52 |
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| author | Azat M. Gabdullin Oleg S. Mozgovoj Rita N. Kadikova Ilfir R. Ramazanov Usein M. Dzhemilev |
| author_facet | Azat M. Gabdullin Oleg S. Mozgovoj Rita N. Kadikova Ilfir R. Ramazanov Usein M. Dzhemilev |
| author_sort | Azat M. Gabdullin |
| collection | DOAJ |
| description | A regioselective method for the preparation of <i>p</i>-tolyl-substituted alkanes is presented based on the reaction of dialkyl-substituted alkynes with four equivalents of TaCl<sub>5</sub> or NbCl<sub>5</sub> in the presence of stoichiometric amounts of metallic magnesium in toluene solution. It was found that the reaction of 5-decyne with the TaCl<sub>5</sub>-M reagent system (where M = Mg, Zn, Fe, Sm, Al, and Mn) in a toluene solution is accompanied by the selective formation of 1-(decan-5-yl)-4-methylbenzene in high yields (79–90%). The effect of solvents on the selectivity of the conversion of 5-decyne under the action of the TaCl<sub>5</sub>-Mg reagent system has been studied. |
| first_indexed | 2024-03-11T06:46:01Z |
| format | Article |
| id | doaj.art-b840e631f3b14235b96e1402bf15e99b |
| institution | Directory Open Access Journal |
| issn | 2673-4583 |
| language | English |
| last_indexed | 2024-03-11T06:46:01Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry Proceedings |
| spelling | doaj.art-b840e631f3b14235b96e1402bf15e99b2023-11-17T10:18:45ZengMDPI AGChemistry Proceedings2673-45832021-11-01815210.3390/ecsoc-25-11680Transformation of Dialkyl-Substituted Alkynes under the Action of the TaCl<sub>5</sub>-Mg and NbCl<sub>5</sub>-Mg Reagent SystemAzat M. Gabdullin0Oleg S. Mozgovoj1Rita N. Kadikova2Ilfir R. Ramazanov3Usein M. Dzhemilev4Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, 450075 Ufa, RussiaInstitute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, 450075 Ufa, RussiaInstitute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, 450075 Ufa, RussiaInstitute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, 450075 Ufa, RussiaInstitute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, 450075 Ufa, RussiaA regioselective method for the preparation of <i>p</i>-tolyl-substituted alkanes is presented based on the reaction of dialkyl-substituted alkynes with four equivalents of TaCl<sub>5</sub> or NbCl<sub>5</sub> in the presence of stoichiometric amounts of metallic magnesium in toluene solution. It was found that the reaction of 5-decyne with the TaCl<sub>5</sub>-M reagent system (where M = Mg, Zn, Fe, Sm, Al, and Mn) in a toluene solution is accompanied by the selective formation of 1-(decan-5-yl)-4-methylbenzene in high yields (79–90%). The effect of solvents on the selectivity of the conversion of 5-decyne under the action of the TaCl<sub>5</sub>-Mg reagent system has been studied.https://www.mdpi.com/2673-4583/8/1/52alkynestantalum (V) chlorideniobium (V) chloridemetallic magnesiumtoluene |
| spellingShingle | Azat M. Gabdullin Oleg S. Mozgovoj Rita N. Kadikova Ilfir R. Ramazanov Usein M. Dzhemilev Transformation of Dialkyl-Substituted Alkynes under the Action of the TaCl<sub>5</sub>-Mg and NbCl<sub>5</sub>-Mg Reagent System Chemistry Proceedings alkynes tantalum (V) chloride niobium (V) chloride metallic magnesium toluene |
| title | Transformation of Dialkyl-Substituted Alkynes under the Action of the TaCl<sub>5</sub>-Mg and NbCl<sub>5</sub>-Mg Reagent System |
| title_full | Transformation of Dialkyl-Substituted Alkynes under the Action of the TaCl<sub>5</sub>-Mg and NbCl<sub>5</sub>-Mg Reagent System |
| title_fullStr | Transformation of Dialkyl-Substituted Alkynes under the Action of the TaCl<sub>5</sub>-Mg and NbCl<sub>5</sub>-Mg Reagent System |
| title_full_unstemmed | Transformation of Dialkyl-Substituted Alkynes under the Action of the TaCl<sub>5</sub>-Mg and NbCl<sub>5</sub>-Mg Reagent System |
| title_short | Transformation of Dialkyl-Substituted Alkynes under the Action of the TaCl<sub>5</sub>-Mg and NbCl<sub>5</sub>-Mg Reagent System |
| title_sort | transformation of dialkyl substituted alkynes under the action of the tacl sub 5 sub mg and nbcl sub 5 sub mg reagent system |
| topic | alkynes tantalum (V) chloride niobium (V) chloride metallic magnesium toluene |
| url | https://www.mdpi.com/2673-4583/8/1/52 |
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