79092-14-1

Upstream product

• 96-09-3 styrene oxide 
• 29680-62-4 Tris(phenylseleno)borane 
• 1666-13-3 diphenyl diselenide 
• 23974-72-3 sodium phenylselenide 
• 106-92-3 Allyl glycidyl ether 
• 122-60-1 Phenyl glycidyl ether 
• 645-96-5 Benzeneselenol 
• 1111071-92-1 phenylselenyl zinc chloride 
• 286-20-4 cyclohexane-1,2-epoxide 

Downstream Products

• 185421-68-5 2-(allyloxy)-1-phenylethyl phenyl selenide 
• 185421-70-9 1-phenyl-2-(2-propynyloxy)ethyl phenyl selenide 
• 102503-71-9 (3S*,4S*)-3-methyl-4-phenyltetrahydrofuran 
• 102503-71-9 trans-4-methyl-3-phenyltetrahydrofuran 
• 102503-71-9 4-methyl-3-phenyltetrahydrofuran 
• 396714-85-5 (E)-3-(2-phenyl-2-phenylselenenyl-ethoxy)-acrylic acid ethyl ester 
• 185421-69-6 2-[(3-methyl-2-butenyl)oxy]-1-phenylethyl phenyl selenide 

Relevant academic research and scientific papers

O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol

A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate “in situ” benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions.

Preparation of the first bench-stable phenyl selenolate: An interesting "on water" nucleophilic reagent

In this communication we report the synthesis and the characterization of the first solid and air-stable selenolates, starting from commercially available phenylselenenyl halides and elemental zinc. These reagents were efficiently employed in the ring ope

Regioselective ring-opening reactions of 1,2-epoxides with thiols and arylselenols directly promoted by [Bmim]BF4

Regioselective ring-opening reactions of 1,2-epoxides with ArSH and ArSeH promoted by ionic liquid [Bmim]BF4 were investigated. A variety of β-hydroxy selenides and β-hydroxy sulfides were obtained in excellent yields (81-99%) with good regiose

A simple zinc-mediated preparation of selenols

Under acidic conditions zinc reduces diselenides to afford selenols, which can be either isolated or treated in situ with alkyl halides to produce alkyl selenides or with epoxides to give β-hydroxyselenides. Georg Thieme Verlag Stuttgart.

Active metallic indium-mediated ring-opening of epoxides with diphenyl diselenides: A novel one-pot synthesis of β-hydroxy selenides in aqueous media

An efficient and simple one-pot procedure for the synthesis of β-hydroxy selenides in aqueous media through highly regioselective ring-opening of epoxides with diphenyl diselenide in the presence of active metallic indium is described.

Stereo- and regioselective zinc-mediated ring-opening of epoxides with diselenides

Two convenient rapid, efficient, stereoselective and highly regioselective methods for the synthesis of β-hydroxy selenides by the direct opening of epoxides with diselenides in acetonitrile in the presence of either Zn/AlCl 3 or zinc powder in

Tetrahydrofuran derivatives from epoxides via group transfer cyclization or reductive radical cyclization of organotellurium and organoselenium intermediates

Monosubstituted epoxides were regiospecifically ring-opened from the sterically least hindered side by benzenetellurolate and benzeneselenolate reagents to afford aryl β-hydroxyalkyl tellurides and selenides, respectively. These materials were O-allylated by treatment with allylic bromides/sodium hydride in tetrahydrofuran and O-prop-2-ynylated when reacted with propargyl bromide/sodium hydride. On photolysis in benzene containing 40 mol % of hexabutylditin, the β-(allyloxy)alkyl aryl tellurides were found to undergo group transfer cyclization to afford 2-substituted 4-[(aryltelluro)methyl]tetrahydrofurans (cis/trans = 1/3-1/10). The aryl β-(prop-2-ynyloxy)alkyl tellurides similarly afforded 2-substituted 4-[(aryltelluro)methylene]tetrahydrofurans with an E/Z-ratio close to unity. The β-(allyloxy)alkyl aryl selenides and aryl β-(prop-2-ynyloxy)alkyl selenides failed to undergo group transfer cyclization. In the presence of tributyltin hydride and 2,2'-azobisisobutyronitrile, the former compounds were found to undergo reductive radical cyclization in high yields to afford 2-substituted 4-methyltetrahydrofurans (cis/trans = 1/3-1/10). Aryl β-(prop-2-ynyloxy)alkyl selenides similarly afforded 2-substituted 4-methylenetetrahydrofurans. 2-Alkoxy-2-(allyloxy)ethyl phenyl selenides, prepared by allyloxyselenenation of vinyl ethers, were found to undergo reductive radical cyclization to afford 2-alkoxy-4-methyltetrahydrofurans (cis/trans = 13-1/4). The preference for formation of trans-2,4-disubstituted tetrahydrofurans in the group transfer and reductive radical cyclizations was rationalized assuming a chairlike transition state with a preferred adoption of a pseudoequatorial position of the 2-substituent. By carrying out the reactions at lower temperatures (ambient or -45°C), using triethylborane as an initiator, it was possible to further increase the trans selectivity in the reductive cyclizations.

Thiol/Diselenide Exchange for the Generation of Benzeneselenolate Ion. Catalytic Reductive Ring-Opening of α,β-Epoxy Ketones

In the presence of N-acetylcysteine sodium salt, benzeneselenolate ion was generated in situ from diphenyl diselenide via thiol/diselenide and thiol/selenenyl sulfide exchange in aqueous methanol under mild conditions.Benzeneselenolate ion thus formed was efficiently alkylated and arylated to afford alkyl phenyl selenides and aryl phenyl selenides, respectively. α,β-Epoxy ketones were catalytically reduced by benzeneselenolate ion to afford β-hydroxy ketones (aldols) in good yields.The stereospecificity of the reaction was demonstrated in the preparation of optically active β-hydroxy ketones from chiral α,β-epoxy ketones.

A convenient procedure for the preparation of organic selenides

Treatment of diphenyl diselenide with tributylphosphine in an alkaline medium forms phenylselenolate ion which converts alkyl halides, α,β-unsaturated ketones, and epoxides into alkyl selenides, (phenylseleno)alkenones, and β-(phenylseleno)alkanols, respe

UNUSUAL REACTIVITY OF SELENOBORANES TOWARDS EPOXIDES: NEW SELECTIVE ROUTES TO β-HYDROXYSELENIDES AND ALLYLALCOHOLS

Selenoboranes react with terminal, α, β- di- and trisubstituted epoxides to produce β-hydroxyselenides (or olefins) in the two first cases and allyl alcohols in the last one.A very high stereodescrimination has been observed for α,β-disubstituted epoxides: the cis epoxide being much more reactive.