Dimethyl sulfoxide-silver tetrafluoroborate

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

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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