112238-64-9

Usage

InChI:InChI=1/C7H5F3O3SSe/c8-7(9,10)14(11,12)13-15-6-4-2-1-3-5-6/h1-5H

Upstream product

• 34837-55-3 Phenylselenyl bromide 
• 2923-28-6 silver trifluoromethanesulfonate 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 1666-13-3 diphenyl diselenide 
• 17697-12-0 benzeneseleninic anhydride 
• 5707-04-0 Phenylselenyl chloride 
• 1493-13-6 trifluorormethanesulfonic acid 

Downstream Products

• 75526-73-7 (2-(phenylselanylmethyl)oxane) 
• 71404-73-4 3-phenylseleno-4-butanolide 
• 112238-70-7 3-hydroxy-4-phenylselenobutanoic acid 
• 112238-71-8 E-4-phenylseleno-3-butenoic acid 
• 1493-13-6 trifluorormethanesulfonic acid 
• 109065-98-7 (2S,3R)-3-Methyl-2-phenylselanylmethyl-tetrahydro-furan 
• 109065-97-6 (2S,3S)-3-Methyl-2-phenylselanylmethyl-tetrahydro-furan 
• 81795-12-2 4.4.7aβ-trimethyl-5β-phenylseleno-2.3.3aα.4.5.6.7.7aβ-octahydrobenzofuran 
• 81795-11-1 (2S,3S)-2-Methyl-2-(4-methyl-pent-3-enyl)-3-phenylselanyl-tetrahydro-furan 
• 81795-11-1 (2S, 3R;3S, 2R) 2-methyl-2-(4-methyl-pent-3-enyl)-3-phenylselenooxolane 
• 132097-56-4 (4aS,6S,8aS)-5,5,8a-Trimethyl-6-phenylselanyl-octahydro-chromene 
• 132097-57-5 3-(2,6,6-Trimethyl-5-phenylselanyl-cyclohex-1-enyl)-propan-1-ol 
• 112238-67-2 3-methyl-5-((phenylselanyl)methyl)dihydrofuran-2(3H)-one 
• 112238-65-0 5-<1-(phenylseleno)ethyl>tetrahydrofuran-2-one 

Relevant academic research and scientific papers

Electrophilic cyclization of allylic 1,1-dimethylisoureas with N-iodosuccinimide and phenylselenenyl triflate

New procedures are described for the cyclization of allylic 1,1-dimethylisoureas. Efficient cyclization of the isoureas to give substituted oxazolines occurs with both N-iodosuccinimide and phenylselenenyl triflate. Reductive dehalogenation can be carried

"Selenium Polonovski Reaction" Using Benzeneselenyl Triflate

Selenoxyammonium salts prepared from tertiary amine N-oxides and benzeneselenyl triflate undergo rearrangement in the presence of triethylamine or DBU to give α-selenoxyamines, which react in situ with an electrophile or nucleophile to afford new secondary or tertiary amine derivatives.

Asymmetric amidoselenenylation of alkenes promoted by camphorselenenyl sulfate: A useful synthetic route to enantiopure oxazolines

Camphorselenenyl sulfate is an efficient chiral, nonracemic electrophilic reagent which can be produced from the easily available camphor diselenide by treatment with ammonium persulfate. This electrophilic selenium reagent reacts with alkenes, at room temperature in acetonitrile, in the presence of water and trifluoromethanesulfonic acid to afford the amidoselenenylation products with moderate facial selectivity. However, the two diastereomeric addition products can be easily separated. After activation of the selenium moiety with phenylselenenyl triflate or with SO2Cl2, these products are deselenenylated stereospecifically by intramolecular substitution and afford enantiomerically pure oxazolines.

Selenirenium and tellurirenium ions

Canted chalcogens: Relatively stable selenirenium salts (R1 2C2SeR)+X- (R1=tert- alkyl) are prepared by reaction of RSe+X- with acetylenes; the bond angle at selenium is only 38°. Highly unstable tellurirenium salts (R12C2TePh)+X- from PhTe+X- and di-tert-alkylacetylenes have a bond angle at tellurium of 34° (see picture). These three-membered-ring cations were experimentally and theoretically investigated. (Chemical Equation Presented).

Diastereo and enantioselective synthesis of 1,2-diols promoted by electrophilic selenium reagents

Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO3H generated "in situ" by oxidation of (PhSe)2 with (NH4)2S2O8 at reflux in a 3:1 mixture of MeCN-H2O. I

Synthesis of enantiomerically pure β-azidoselenides starting from natural terpenes

Several unsaturated natural terpenes have been easily converted, in good yields, into the corresponding enantiomerically pure β-azidoselenides by addition of the electrophilic selenium reagent PhSeOTf in the presence of sodium azide. These reactions are stereospecific anti additions, which occur with a Markovnikov orientation. Examples of the synthetic importance of these β-azidoselenides are also reported.

Introduction of cis-vicinal amino alcohol functionality into the cyclohexane ring employing (1S,2S)-2-amino-1,2-diphenylethanol: Synthesis of enantiopure aminocyclohexitols

Pd(0)-catalyzed allylic amination of 3-bromocyclohexene with (1S,2S)-2-amino-1,2-diphenylethanol and subsequent intramolecular oxyselenenylation of the resulting allylic amine 6 followed by oxidation-elimination afforded the valuable cis-fused bicyclic olefin 10. Oxyselenenylation of cyclohexene with (1S,2S)-N-(benzyloxycarbonyl)-2-amino-1,2-diphenylethanol and subsequent oxidation-elimination gave the allylic ether 18. Intramolecular aminoselenenylation of 18 followed by oxidation-elimination provided the cis-fused bicyclic olefin 21, which is the regioisomer of 10. Further stereoselective transformation of 10 afforded enantiopure aminocyclohexitols.

De novo synthesis of a methylene-bridged Neu5Ac-α-(2,3)-Gal C-disaccharide

A general strategy toward the synthesis of C-ketosides of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of methylene-bridged Neu5Ac-α-(2,3)-Gal C-disaccharide 2. The key strategic element of this novel approach is a stereoselective, 6-exo-trig selective, electrophilic cyclization of the appropriate open chain precursor 4 by means of phenylselenyl triflate. The open chain precursor was formed by the addition of lithiated iodide 18 accessible from D-galactose to open chain aldehyde 5a obtained from D-glucono-δ-lactone by chain elongation. Subsequent C1-incorporation using Tebbe-reagent, formation of a cyclic carbonate, and deprotection of the two isopropylidene ketals afforded tetrol 4 which, upon treatment with phenylselenyl triflate, was stereoselectively cyclized in a 6-exo-trig selective manner. A selena-Pummerer rearrangement, oxidation, and esterification readily led to methyl ester 37 which, after deacetylation, could be regioselectively tetrabenzoylated with benzoyl cyanide. Triflate activation of the axial hydroxyl group in 40 and nucleophilic displacement by azide ion with inversion of configuration afforded azide 41, which was reduced with hydrogen and Pearlman's catalyst. Concomitant removal of the benzyl ethers and subsequent saponification of all ester moieties successfully completed the de novo synthesis of the desired methylene bridged Neu5Ac-α-(2,3)-Gal C-disaccharide 2.

The reaction of phenylselenenyl triflate with diazo compounds

The reaction of phenylselenenyl triflate with diazo compounds is described. Diazoalkanes, α-diazoketones and α-diazoesters gave the corresponding di(phenylselanyl) derivatives either at 0 °C or at room temperature, α-Diazo-β-dicarbonyl compounds gave selectively di(phenylselanyl) derivatives at - 78 °C, while they gave a mixture of di(phenylselanyl)- and mono(phenylselanyl) derivatives either at 0 °C or at room temperature.

Stereoselective Cyclization of 4-Substituted 5-Hexen-1-ols and Related Compounds by Benzeneselenenyl Triflate

Oxyselenylation of 4-substituted 5-hexen-1-ols 1 with benzeneselenenyl trifluoromethanesulfonate proceeds by intramolecular exo cyclization stereoselectively to give 3-substituted trans- or cis-2-(phenylselenenylmethyl)tetrahydropyrans 3.Formation of the trans isomers is favored when the substituents contain alkyl or phenyl substituents in the 4-position, whereas the cis isomers predominate when the substituents are alkoxyalkyl, alkoxyl, acyl, and hydroxyl.The mechanism of the trans and cis stereoselectivity is explained by steric and electronic effects in the phenylseleniranium intermediates, 7 and 8. - Key Words: Oxyselenenylation / Benzeneselenenyl triflate / Selenium compounds / Trifluoromethanesulfonate / Alkenols