98607-00-2Relevant academic research and scientific papers
Remarkable alkene-to-alkene and alkene-to-alkyne transfer reactions of selenium dibromide and phsebr. Stereoselective addition of selenium dihalides to cycloalkenes
Potapov, Vladimir A.,Musalov, Maxim V.,Kurkutov, Evgeny O.,Yakimov, Vladimir A.,Khabibulina, Alfiya G.,Musalova, Maria V.,Amosova, Svetlana V.,Borodina, Tatyana N.,Albanov, Alexander I.
, (2020/01/13)
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 SeBr2 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 SeBr2 and PhSeBr transfer reagents are Se(CH2CH2Br)2 and PhSeCH2CH2Br, 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 SeBr2 and PhSeBr transfer reactions which proceeded with higher selectivity compared to analogous addition reactions of SeBr2 and PhSeBr to alkynes under the same conditions.
A convenient synthetic method of β-bromo alkenyl phenyl selenides by the reaction of alkynes with diphenyl diselenide and copper(II) bromide
Nishiyama, Yutaka,Ohnishi, Haruko,Iwamoto, Masako,Sonoda, Noboru
experimental part, p. 1021 - 1024 (2010/07/08)
When alkynes were allowed to react with diphenyl diselenide in the presence of copper(II) bromide, bromophenylselenation of the carbon-carbon triple bond smoothly proceeded to give the corresponding -bromo alkenyl phenyl selenides in moderate to good yields. Similarly, chlorophenylselenation of alkynes occurred by the use of copper(II) chloride as a copper salt giving β-chloro alkenyl phenyl selenides in good yields. Copyright Taylor & Francis Group.
