51533-23-4Relevant articles and documents
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
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.
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
