78837-70-4Relevant academic research and scientific papers
Oxidative Cleavage of Diselenide by m-Nitrobenzenesulfonyl Peroxide. Novel Method for the Electrophilic Benzeneselenenylations of Olefins and Aromatic Rings
Yoshida, Masato,Sasage, Shuichi,Kawamura, Kyoko,Suzuki, Takashi,Kamigata, Nobumasa
, p. 416 - 422 (2007/10/02)
Diphenyl diselenide was found to be readily converted into benzeneselenenyl-m-nitrobenzenesulfonate (PhSeOSO2C6H4NO2-m) by treating with m-nitrobenzenesulfonyl peroxide.When the selenenyl sulfonate thus formed was allowed to react in situ with olefins, such as cyclohexene, 1-octene, or styrene, in the presence of various nucleophiles, the adducts of benzeneselenenyl group and a nucleophile were obtained.As the nucleophiles water, methanol, acetic acid, phenol, and anisole could be employed; oxyselenenylated : R=H, Me, Ac, and Ph) and arylselenenylated : R=H and Me) adducts were afforded.Phenol gave oxyselenenylated products in cyclohexene or 1-octene and arylselenenylated products in styrene.Efficient intramolecular cyclizations of unsaturated alcohols and carboxylic acids were similarly performed by the selenenyl sulfonate to afford corresponding benzeneselenenylated cyclic ethers and lactones.The selenenyl sulfonate was also found to be a highly reactive benzeneselenenylating reagent for aromatic rings, such as anisole, phenol, acetanilide, toluene, and benzene.
The Stereochemistry of a Substitution Reaction via an Episelenonium Ion: Retention by a 2-Pyridylseleno Group versus Scrambling by a Phenylseleno Group
Toshimitsu, Akio,Ito, Masaaki,Uemura, Sakae
, p. 530 - 531 (2007/10/02)
The first example of retention of configuration during substitution on a carbon atom situated β to an arylseleno group was discovered when using a 2-pyridylseleno (2-PySe) group.
PHENYLSELENO-LACTONIZATION OF OLEFINIC NITRILES PROMOTED BY PEROXYDISULPHATE ION OXIDATION OF DIPHENYL DISELENIDE
Tiecco, Marcello,Testaferri, Lorenzo,Tingoli, Marco,Bartoli, Donatella
, p. 6819 - 6832 (2007/10/02)
The oxidation of diphenyl diselenide with ammonium peroxydisulphate is a very simple and efficient method to produce phenylselenium cations in the absence of nucleophilic counter ions.The reaction carried out in the presence of an olefin, in acetonitrile
Amidoselenation of Olefins and Its Utilization for Synthesis of Allylic Amides
Toshimitsu, Akio,Aoai, Toshiaki,Owada, Hiroto,Uemura, Sakae,Okano, Masaya
, p. 4727 - 4733 (2007/10/02)
The reaction of phenylselenyl chloride with olefins in acetonitrile containing trifluoromethanesulfonic acid and water affords β-acetamidoalkyl phenyl selenides in good to excellent yields.This represents the first example of one-pot amidoselenation of mono- and disubstituted olefins.The reaction can be carried out in benzonitrile, propionitrile, butyronitrile, or ethyl cyanoacetate.It was confirmed that the amidoselenation reaction proceeds with trans stereospecifity.Oxidative elimination of the produced β-amidoalkyl phenyl selenides gives allylic amides selectively in good to excellent yields.These two reactions constitute a good method for conversion of olefins to allylic amides.
