51533-23-4Relevant academic research and scientific papers
77Se, 13C and 1H NMR Spectra of Phenylselenenyl Azide and Chloride Addition Products of Methylenecyclohexane and Cyclohexene
Boyko, Walter J.,Duarte, Franco J.,Giuliano, Robert M.
, p. 259 - 262 (1994)
The 77Se, 13C and 1H NMR spectra of the products of phenylselenenyl azide and chloride additon to methylenecyclohexane and cyclohexene are presented.Scalar couplings between 77Se and 1H/13C allowed the absolute assignment of the regioisomers in the 1H and
The Electrochemical cis-Chlorination of Alkenes
Strehl, Julia,Fastie, Cornelius,Hilt, Gerhard
supporting information, p. 17341 - 17345 (2021/10/23)
The first example for the electrochemical cis-dichlorination of alkenes is presented. The reaction can be performed with little experimental effort by using phenylselenyl chloride as catalyst and tetrabutylammoniumchloride as supporting electrolyte, which also acts as nucleophilic reagent for the SN2-type replacement of selenium versus chloride. Cyclic voltammetric measurements and control experiments revealed a dual role of phenylselenyl chloride in the reaction. Based on these results a reaction mechanism was postulated, where the key step of the process is the activation of a phenylselenyl chloride-alkene adduct by electrochemically generated phenylselenyl trichloride. Like this, different aliphatic and aromatic cyclic and acyclic alkenes were converted to the dichlorinated products. Thereby, throughout high diastereoselectivities were achieved for the cis-chlorinated compounds of >95 : 5 or higher.
Catalytic, stereospecific syn-dichlorination of alkenes
Cresswell, Alexander J.,Eey, Stanley T.-C.,Denmark, Scott E.
, p. 146 - 152 (2015/03/04)
As some of the oldest organic chemical reactions known, the ionic additions of elemental halogens such as bromine and chlorine to alkenes are prototypical examples of stereospecific reactions, typically delivering vicinal dihalides resulting from anti-addition. Although the invention of enantioselective variants is an ongoing challenge, the ability to overturn the intrinsic anti-diastereospecificity of these transformations is also a largely unsolved problem. Here, we describe the first catalytic, syn-stereospecific dichlorination of alkenes, employing a group transfer catalyst based on a redox-active main group element (selenium). With diphenyl diselenide (PhSeSePh) (5amol%) as the pre-catalyst, benzyltriethylammonium chloride (BnEt 3 NCl) as the chloride source and an N-fluoropyridinium salt as the oxidant, a wide variety of functionalized cyclic and acyclic 1,2-disubstituted alkenes, including simple allylic alcohols, deliver syn-dichlorides with exquisite stereocontrol. This methodology is expected to find applications in streamlining the synthesis of polychlorinated natural products such as the chlorosulfolipids.
Iodide-promoted deselenylation of β-chloro-and β-oxyselenides to form alkenes and selenenyl iodides
Sase, Shohei,Ebisawa, Kazuaki,Goto, Kei
supporting information; experimental part, p. 766 - 768 (2012/09/22)
Deselenylation reaction of β-chloro-and β-oxyselenides proceeded efficiently by treatment with tetrabutylammonium iodide (TBAI) to afford alkenes in good yields. It was established that selenenyl iodides were formed in these reactions. Catalytic transformation of β-chloro-and β-oxyselenides to alkenes was also developed.
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 ALLYLIC SULPHIDES AND SELENIDES BY LEWIS ACID MEDIATED DISPLACEMENT REACTIONS OF SULPHONES
Simpkins, Nigel S.
, p. 6787 - 6790 (2007/10/02)
Allylic sulphides or selenides are produced by reaction of appropriate α-sulphonyl sulphides or selenides with allyltrimethylsilane in the presence of EtAlCl2.
ALKENE CARBOSULPHENYLATION AND CARBOSELENYLATION: THE USE OF ALLYLTRIMETHYLSILANE AND O-SILYLATED ENOLATES.
Alexander, Rikki P.,Paterson, Ian
, p. 5911 - 5914 (2007/10/02)
Allyltrimethylsilane, as well as O-silylated enolates, can be alkylated by the PhSCl adducts of alkenes and vinyl ethers (1, X=SPh); the PhSeCl analogues (1, X=SePh), however, are less useful for alkylation purposes due to competing nucleophilic attack at selenium.
