71404-75-6

Upstream product

• 1577-22-6 5-hexenoic acid 
• 1666-13-3 diphenyl diselenide 
• 112238-64-9 phenylselenyl triflate 
• 133708-80-2 benzeneselenenyl m-nitrobenzenesulfonate 
• 5707-04-0 Phenylselenyl chloride 
• 5048-19-1 hex-5-enenitrile 
• 28487-09-4 hex-5-enamide 
• 87281-54-7 N-benzylhex-5-enamide 

Relevant academic research and scientific papers

Time-economical synthesis of selenofunctionalized heterocycles via I2O5-mediated selenylative heterocyclization

A time-economical and robust synthesis of various selenofunctionalized heterocycles was accomplished via I2O5-mediated selenocyclizations of olefins with diselenides. Using this method, 116 selenomethyl-substituted heterocycles were

Electrochemical Difunctionalization of Olefines: Access to Selenomethyl-Substituted Cyclic Ethers or Lactones

A metal- and oxidant-free electrochemical method for preparing selenomethyl-substituted cyclic ethers or lactones via difunctionalization of olefines is presented. A series of selenomethyl-substituted cyclic ethers, particularly 9- and 11- membered, selen

Preparation of Heterocycles via Visible-Light-Driven Aerobic Selenation of Olefins with Diselenides

The aerobic dehydrogenative cyclization of alkenes with easily accessible diselenides facilitated by visible light is reported. Notably, the features of this transition-metal-free protocol are pronounced efficiency and practicality, good functional group

Acidic hierarchical zeolite ZSM-5 supported Ru catalyst with high activity and selectivity in the seleno-functionalization of alkenes

The acidic hierarchical zeolite ZSM-5 (HZSM-5-H) was synthesized for the preparation of a supported Ru catalyst (Ru/HZSM-5-H). The obtained Ru/HZSM-5-H catalyst shows high activity and product selectivity in the seleno-functionalization of alkenes compared to γ-Al2O3, basic ETS-10 and acidic microporous zeolite ZSM-5 supported Ru catalysts (Ru/γ-Al2O3, Ru/ETS-10 and Ru/HZSM-5, respectively), as well as a homogeneous RuCl3 catalyst. The relatively strong acidic sites in Ru/HZSM-5-H could benefit the adsorption of styrenes and the activation of the CC bond. Meanwhile, Ru4+ in Ru/HZSM-5-H could facilitate the formation of electrophilic selenium species as compared to Ru0 species. In addition, the Ru/HZSM-5-M catalyst exhibits broad substrate compatibility in the difunctionalization of alkenes.

Ammonium Iodide Catalyzed Selenolactonization of Unsaturated Acids

A convenient procedure is developed for the preparation of selenolactones from unsaturated acids and diselenides using a catalytic amount of ammonium iodide in combination with m-chloroperoxybenzoic acid as the oxidant. This catalytic ring-closing method

Oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). A new method for the electrophilic phenylselenenylation of alkenes under mild conditions

The oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) represents a convenient mild method to produce a strongly electrophilic phenylselenium reagent. Clean phenylseleno methoxylations and hydroxylations of alkenes containing different types of functional groups can be effected by working in methanol or in acetonitrile and water, respectively. This new electrophilic reagent can also be employed to promote efficient cyclization reactions of alkenols to tetrahydrofurans or of alkenoic acids to lactones.

The Cyclization of Hex-5-enylcarbamates and Related Compounds with Benzeneselenyl chloride and Some Reactions of the 2-Substituted Piperidine Products

The reaction of hex-5-enylcarbamates with benzeneselenyl chloride gives adducts which cyclize in the presence of silica or stannic chloride, to 2-phenylselenomethylpiperidine derivatives which are unstable, both thermally and on silica.The selenoxides also undergo a Pummerer-type reaction to form 2-acetoxy(phenylseleno)methylpiperidine systems which can be oxidatively converted into a piperidine 2-aldehyde.The selenoxides react with carbon tetrachloride in base to form a 2,2,2-trichloroethyl substituent.Both the selenoxides and the phenylseleno groups of the cyclized products can be displaced by nucleophiles.Ethy hept-6-enylcarbamate did not give a cyclic product with benzeneselenyl chloride and silica, and gave a poor yield of a hexahydroazepine with stannic chloride.Hex-5-enamide cyclized to give a lactone, rather than a lactam, product.Hex-5-enenitrile gave Ritter reaction products with benzeneselenyl chloride in acetonitrile, and a dimer in non-nucleophilic solvents.

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.

Electrochemical cyclization of unsaturated hydroxy compounds. Phenylselenoetherification and phenylselenolactonization

Phenylselenoetherification and phenylselenolactonization were performed in one step by electrolysis of unsaturated alcohols or carboxylic acids and diphenyl diselenide in organic solvent containing halide ions as mediators.

Stereoselective Selenolactonization by Superelectrophilic Benzeneselenenyl Triflate

Benzeneselenenyl triflate is prepared from benzeneselenenyl chloride and silver trifluoromethanesulfonate.It performs selenium-induced cyclization of β,γ-, γ,δ-, and δ,ε-unsaturated carboxylic acids.