Sulfoxide-Silver Tetrafluoroborate

Solubility DMSO sol H2O, alcohol, acetone, THF, CH2CI2. P2O5 sol H2O. 

Form Supplied in DMSO is a colorless liquid widely available, including anhydrous gradesofDMSOpackedunderN2 P205 (more accurately P4O10) is a white crystalline solid widely available. 

Preparative Method the active oxidant, formulated as Me2+ S0(P205) , is generated in situ from the reaction of DMSO and P2O5 in the presence of the alcohol. 

Purihcation DMSO distillation from CaH2 at 56-57 (2/5 mmHg or 83-85 °(2/17 mmHg storage over 3A molecular sieves. P2O5 sublimation. 

Related Reagents. iV-Chlorosuccinimide-Dimethyl Sulfide Chromic Acid Dimethyl Sulfide-Chlorine Dimethyl Sulfoxide-Acetic Anhydride Dimethyl Sulfoxide-Dicyclohexylcarbo-diimide Dimethyl Sulfoxide-Methanesulfonic Anhydride Dimethyl Sulfoxide-Oxalyl Chloride Dimethyl Sulfoxide-Sulfur Trioxide/Pyridine Dimethyl Sulfoxide-Trifluoroacetic Anhydride Dimethyl Sulfoxide-Triphosgene Manganese Dioxide Pyridinium Chlorochromate Pyridinium Dichromate Ruthenium(IV) Oxide Silver(I) Carbonate on Celite 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3( l/ -one. 

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Dimethyl Sulfoxide-Iodine, 233 Dimethyl Sulfoxide-Methanesulfonlc Anhydride, 234 Dimethyl Sulfoxide-Phosphorus Pentoxlde, 234 Dimethyl Sulfoxide-Silver Tetrafluoroborate, 235... 

In their important work on the synthesis and properties of optically active chlorosulfurane (+)-177, Martin and Balthazor (195) deduced its absolute configuration by means of chemical correlations. Reaction of (+)-l 77 with silver tetrafluoroborate yields cyclic sulfonium salt 198, which was hydrolyzed without isolation under alkaline conditions to give sulfoxide (-)-(5 -180, from which (+)-177 was obtained. Assuming that the conversion (+)-l 77 -> 198 proceeds with... 

Alkylation of several thietane 1-oxides has been accomplished by treatment of the sulfoxide with trimethyl- or triethyloxonium tetrafluoroborate/ or hexa-chloroantimonate or with methyl iodide-silver tetrafluoroborate. Non-nucleophilic anions are preferred to avoid ring opening. 

Complexes. Silver tetrafluoroborate is insoluble in cyclohexane but very soluble in water, ether, toluene, and nitromethane, and moderately soluble in benzene and cyclohexene. - Solubility in the unsaturated hydrocarbons is attributed to n-bond formation between the unsaturated compound and silver ion. Complexes have been observed with both ir-electron donors and lone-pair donors thus Meerwein prepared stable complexes with benzene, mesitylene, cycloheptatriene, diethyl ether, dimethyl sulfoxide, and a series of acid nitriles. However, the silver tetrafluoroborate-benzene complex is reported variously as a 1 1 complex, a 1 2 complex, and as a 2 3 complex. ... 

Komblum s method of oxidation with dimethyl sulfoxide. 3-Nortricyclyl bromide (1) was added to a solution of an equivalent amount of silver tetrafluoroborate in dimethyl sulfoxide, whereupon silver bromide began to precipitate. After 1 hr.. 

The ketone 373 was synthesized from three different starting materials. Reacjtion, of the bromide 234 or the chloride 235 with silver tetrafluoroborate in dimethyl 1 sulfoxide at 70° gave the ketone 373 in 79% and 75% yield, resp. In both cases alpoj alcohol 236 was formed as by-product (8% and 20%, resp.). Oxidation of the alcohpl 236 with CrOs/pyridine gave in moderate yield the ketone 373, too. The latter wbsj reduced by LiAlHi to a mixture of the two C(10)-epimeric alcohols IQffo of the I 10 -alcohol 301 (3.2.4.) [also characterized as its acetate 266 (3.2.3.)] and 21% of the 10 -alcohol25d. 

OXIDATION, REAGENTS Acetyl nitrate. Bis(tri-n-butyltin)oxide. Bromine-Hexameth-ylphosphoric triamide. f-Butyl perbenzoate. Ceric ammonium nitrate. N-chlorosuc-cinimide-Dimethyl sulfide. Chromic add. Chromic anhydride. Chromic anhydride-Acetic anhydride. Chromic anhydride-Hexamethylphosphoric triamide. 2,3-Dichloro-5,6-dicyano-l,4-benzoquinone. Dimethyl sulfoxide. Dimethyl sulfoxide-Trifluoro-acetic anhydride. Diphenylseleninlc anhydride. Iodine tris(trifluoroacetate). Lead tetraacetate. N-Methylmorpholine -N-oxide. p-NitrobenzenesulfonyI peroxide. Oxygen, singlet. Palladlumfll) chloride. Peroxybcnzimidic acid. Phenylseleninyl chloride. N-Phenyl-l,2,4-triazoline-3,5-dione. Potassium chromate. Potassium superoxide. Pyri-dinium chlorodiromate. Salcomine. Silver carbonate-Celite. Sodium hypochlorite. Sulfuryl chloridc-Silica gel. Thallium(III) acetate. ThaUium(III) nitrate. Triphenyl phosphite ozonide. Trltyl tetrafluoroborate. Uranium hexafluoride. 

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