Peroxytrifluoroacetic acid oxidation of sulfides to sulfoxides and sulfones

Abstract

PS-100 spectrometer, and the samples contained Me4Si as internal standards.(1) (l-Bromo-2,2,2-trifluoroethyl)sulfur Pentafluoride. In a typical reaction a 10-mL stainless-steel Hoke cylinder was charged with 10 mmol of SF5CH=CF2 and 11.5 mmol of Br2 and then placed in a 110 °C oven for 24 h. The cylinder was cooled to room temperature and the volatile material condensed onto Hg contained in a 50-mL Pyrex reactor to remove unreacted Br2. After being shaken for 10 min, the remaining mixture was fractionated by °C trap was empty, and the -80 and -95 °C traps contained impure product. The -196 °C trap contained 1.5 mmol of a material identified as FCH(Br)CF3. The -80 and -95 °C traps were combined, and final purification accomplished by gas chromatography, yielding 6.17 mmol (61.7%) of SF6CH(Br)CF3.

Sulfilimines and Sulfoximines by Reaction of Nitriles with Perfluoroalkyl Sulfoxides

“…Amongst the classical reagents tested, disappointing results (partial transformations, lack of selectivity) occurred with metachloroperbenzoic acid, trifluoroperacetic acid, ruthenium dioxide and hydrogen peroxide. [22][23][24][25] We were pleased to observe that the cheap and nontoxic potassium permanganate was the candidate of choice. [26] The controlled oxidation of sulfilimines has been undertaken with excellent to modest (due to incomplete conversion of the starting material) yields depending on substrate (Table 3, entries 1-4).…”

Green route for selective gram‐scale oxidation of sulfides using tungstate/triazine‐based ionic liquid immobilized on magnetic nanoparticles as a phase‐transfer heterogeneous catalyst

“…The use of large amounts of highvalent oxidizing agent, production of unwanted toxic waste and by-products, difficult and time-consuming separation and purification of desired product from reaction mixture [9] and, importantly, overoxidation of sulfoxides to sulfones are some examples. [10] H 2 O 2 has been found to be an efficient and green promising oxidant for sulphides [11] because it offers benefits such as low cost, high content of active oxygen and production of water as environmentally benign by-product. [12] Several transition metals have been also applied in order to increase activity and selectivity of hydrogen peroxide for sulfide oxidation.…”

The efficient and chemoselective MoO3-catalyzed oxidation of sulfides to sulfoxides and sulfones with H2O2

“…As the sulfoxides are important for carbon-carbon bond formation and functional group transformation, the search for new methods for the selective oxidation of sulfides to sulfoxides continues despite the existence of a number of methods available for this transformation. Selective oxidation of sulfides to sulfoxides and sulfones with the same reagent system under adjusted reaction conditions is an important process in synthetic organic chemistry and only a few reports are available in the literature (8)(9)(10)(11)(12)(13).…”