| Autor: |
Potapov VA; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia., Musalov MV; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia., Kurkutov EO; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia., Yakimov VA; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia., Khabibulina AG; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia., Musalova MV; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia., Amosova SV; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia., Borodina TN; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia., Albanov AI; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia. |
| Abstrakt: |
The original goal of this research was to study stereochemistry of selenium dihalides addition to cycloalkenes and properties of obtained products. Remarkable alkene-to-alkene and alkene-to-alkyne transfer reactions of selenium dibromide and PhSeBr were discovered during this research. The adducts of selenium dibromide with alkenes or cycloalkenes easily exchange SeBr 2 with other unsaturated compounds, including acetylenes, at room temperature, in acetonitrile. Similar alkene-to-alkene and alkene-to-alkyne transfer reactions of the PhSeBr adducts with alkenes or cycloalkenes take place. The supposed reaction pathway includes the selenium group transfer from seleniranium species to alkenes or alkynes. It was found that the efficient SeBr 2 and PhSeBr transfer reagents are Se(CH 2 CH 2 Br) 2 and PhSeCH 2 CH 2 Br, which liberate ethylene, leading to a shift in equilibrium. The regioselective and stereoselective synthesis of bis( E -2-bromovinyl) selenides and unsymmetrical E- 2-bromovinyl selenides was developed based on the SeBr 2 and PhSeBr transfer reactions which proceeded with higher selectivity compared to analogous addition reactions of SeBr 2 and PhSeBr to alkynes under the same conditions. |
