63831-75-4Relevant 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.
Reactions of areneselenenamides with alkenes in the presence of phosphorus(V) and sulfur(IV) oxyhalides. New synthesis of β-Haloalkyl Selenides
Antipin,Klak,Beloglazkina,Zyk
experimental part, p. 842 - 847 (2009/12/09)
A new procedure was proposed for activation of areneselenenamides with phosphorus(V) and sulfur (IV) oxyhalides. According to the 1H, 13C, and 31P NMR data, areneselenenamide reacts with phosphorus oxyhalide to form interm
Synthesis of azetidine and pyrrolidine derivatives through selenium-induced cyclization of secondary homoallylamines - A 77Se NMR study
Pannecoucke, Xavier,Outurquin, Francis,Paulmier, Claude
, p. 995 - 1006 (2007/10/03)
Treatment of α-alkyl and α,α-dialkyl homoallylic amines 1 with PhSeX (X = C1, Br, I), in CH3CN containing sodium carbonate produced mixtures of azetidines 2 and pyrrolidines 3. The cyclization also occurred in the absence of Na2CO3, and the corresponding azetidinium and pyrrolidinium salts 2(HX) and 3(HX) were formed in CDCl3 or CH3CN. The crude reaction mixtures were analysed by 77Se NMR. Each product - 2, 3, 2(HX), and 3(HX) - was characterized by its 77Se chemical shift, and the product ratios were determined for each reaction. The ratios of azetidine 2 to pyrrolidine 3 increased not only according to the steric hindrance around the α-carbon, but also with the nature of the counterion X- (PhSeCl 1, R2 ≠H), produced only the azetidinium salts 2(HI), allowing the isolation of the corresponding azetidines 2, albeit in poor yield. Some reactions were monitored by 77Se NMR at the beginning of the addition-cyclization process. No intermediates were observed when PhSeI was used, but the thermodynamic addition products 5(Br), 5(HBr), and some dibromoselenuranes 8 were detected. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
