247129-88-0 | Diphenylvinylsulfonium Triflate

CAS:247129-88-0 | Diphenylvinylsulfonium Triflate,Description

Diphenyl(vinyl)sulfonium trifluoromethanesulfonate is a derivative of sulfonic acid and can be used as an organic reagent. It can be used as a raw material for organic synthesis with styrene derivatives to synthesize 2-arylazo pyridine at low temperature.

Molecular Structure Analysis

The InChI code for Diphenyl(vinyl)sulfonium trifluoromethanesulfonate is 1S/C14H13S.CHF3O3S/c1-2-15(13-9-5-3-6-10-13)14-11-7-4-8-12-14;2-1(3,4)8(5,6)7/h2-12H,1H2;(H,5,6,7)/q+1;/p-1.

Scientific Research Applications

Preparation and reactions of β-trifluoromethyl vinyl sulfonium salt

This crystalline reagent, derived from diphenyl iodonium salt, showcased versatile transformations such as aziridination and vinylation, generating trifluoromethylated compounds with excellent yields (Maeda et al., 2010).

Epoxy-annulations with alpha-amido ketones

Diphenyl vinyl sulfonium salt underwent highly diastereoselective epoxy-annulation reactions with chiral amido-ketones. The process was influenced more by the reagent's chirality than the substrate, enabling kinetic resolution of racemic amido-ketones (Unthank et al., 2008).

Advanced Chemical Reactions

Synthesis of trifluoromethylated cyclopropane derivatives

(E)-Diphenyl-β-(trifluoromethyl)vinylsulfonium triflate was used for double alkylation with active methylene compounds, yielding trifluoromethylated cyclopropane derivatives efficiently. These derivatives underwent further transformations to create complex structures like trifluoromethylated dihydroaminothiophene and aminothiophene (Kasai et al., 2012).

Cyclopropanation of oxindoles

Zinc triflate-mediated cyclopropanation of oxindoles using vinyl diphenyl sulfonium triflate showcased high yields, tolerance to a wide range of functional groups, and potential for late-stage functionalization of complex molecules (Zhou et al., 2017).

Membrane Technology and Conductivity

Sulfonated polyimide/protic ionic liquid composite membranes

The use of ionic liquids with vinyl groups, like 1-vinylimidazolium trifluoromethanesulfonate, in preparing composite membranes significantly enhanced the conductivity of proton exchange membranes. These materials are crucial for applications like fuel cells (Chen et al., 2013).

Safety And Hazards

Diphenyl(vinyl)sulfonium trifluoromethanesulfonate is associated with several hazards. It is recommended to avoid dust formation, breathing mist, gas or vapours, and contact with skin and eyes. Use of personal protective equipment and chemical impermeable gloves is advised. Ensure adequate ventilation and remove all sources of ignition. In case of a spill or leak, evacuate personnel to safe areas and keep people away from and upwind of the spill/leak.

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