77037-09-3

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 111-66-0 oct-1-ene 
• 75-05-8 acetonitrile 
• 1666-13-3 diphenyl diselenide 
• 124439-87-8 (R)-1-(phenylseleno)-2-octanol 
• 23974-72-3 sodium phenylselenide 
• 77495-66-0 (R)-1,2-epoxyoctane 

Relevant academic research and scientific papers

Intramolecular nucleophilic deselenenylation reactions promoted by benzeneselenenyl triflate. Stereospecific synthesis of vicinal amino alcohol precursors

After activation with electrophilic selenenylating agents, the phenylseleno group of vicinal azido selenides, containing internal oxygen or nitrogen nucleophilic substituents, readily undergoes intramolecular nucleophilic displacement to afford azido-substituted heterocyclic compounds. This intramolecular substitution occurs with inversion of configuration at the carbon atom bearing the selenium atom. Starting from acetamido selenides and carbamato selenides, a stereocontrolled synthesis of the vicinal amino alcohol precursor oxazolines and oxazolidin-2-ones has been developed.

Oxidative Cleavage of Diselenide by m-Nitrobenzenesulfonyl Peroxide. Novel Method for the Electrophilic Benzeneselenenylations of Olefins and Aromatic Rings

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

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

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

Novel Method for Electrophilic Selenenylation Using Diselenide with Nitrobenzenesulfonyl Peroxide

Diphenyl diselenide could be readily converted into cationic selenenylating reagent by treating with m-nitrobenzenesulfonyl peroxide, and the intermediate was reacted with olefins in the presence of methanol, phenol, or electorn-rich benzenes in one pot to afford methoxy-, phenoxy-, or arylselenenylated compounds, respectively.

Amidoselenation of Olefins and Its Utilization for Synthesis of Allylic Amides

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.

Anodic acetamidoselenation of alkenes

Anodic oxidation of diphenyldiselenide in acetonitrile in the presence of an alkene gives acetamidoselenides.