112238-64-9

Basic information

• Product Name: benzeneselenyl trifalate
• Synonyms: benzeneselenyl trifalate
• CAS NO: 112238-64-9
• Molecular Formula: C₇H₅F₃O₃SSe
• Molecular Weight: 305.13
• Mol File: 112238-64-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 280.6°Cat760mmHg
• Flash Point: 123.5°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.00639mmHg at 25°C
• CAS DataBase Reference: benzeneselenyl trifalate(CAS DataBase Reference)
• NIST Chemistry Reference: benzeneselenyl trifalate(112238-64-9)
• EPA Substance Registry System: benzeneselenyl trifalate(112238-64-9)

Safety Data

• Hazardous Substances Data: 112238-64-9(Hazardous Substances Data)

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) 
• 70188-06-6 6-ethenyl-2,2,6-trimethyl-3-(phenylseleno)tetrahydropyran 
• 132097-58-6 ((1R,4aS,6R,8aR)-2,5,5,8a-Tetramethyl-6-phenylselanyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-methanol 
• 75826-35-6 dihydro-5-methyl-5-<(phenylseleno)methyl>-2(3H)-furanone 
• 113423-62-4 (2S,3R)-2-Phenylselanylmethyl-tetrahydro-pyran-3-ol 

Relevant articles and documents

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

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).

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.