Methyl Sulfoxide

A mixture of 100 ml of glacial acetic acid, 15 ml of 30% hydrogen peroxide and 5.0 g of allenyl methyl sulfoxide (see Chapter VII-1, Exp. 1) was heated for 30 min at 100°C. The colourless solution was cooled to 20°C and poured into 300 ml of ice-water. The sulfone was isolated by extracting the solution twelve times... 

Chemical Designations - Synonyms DMSO Methyl Sulfoxide Chemical Formula CH3SOCH3. Ohservahle Characteristics - Physical State (as normally shipped) Liquid Color Colorless Odor Slight almost odorless. 

Common Nama Methyl sulfoxide Structural Formula (CH3)2SO Chamical Abstracts Registry No. 67-68-5... 

The facile and selective oxidation of both primary and secondary hydroxy groups with certain nucleotides led Pfitzner and Moffatt (48) to explore the scope of the carbodiimide-methyl sulfoxide reagent with steroid and alkaloid alcohols. Relatively minor differences were apparent in the rate of oxidation of epimeric pairs of 3- and 17- hydroxy steroids whereas the equatorial lLx-hydroxyl group in several steroids was readily oxidized under conditions where the axial epimer was unreactive [cf. chromic oxide oxidation (51)]. 

The mechanism of the oxidation reaction, resulting from treatment of an alcohol with dicyclohexylcarbodiimide and methyl sulfoxide in the presence of a proton source, was elucidated by isotope experiments (24). These confirmed that the reaction proceeded by formation of a... 

Following closely on the foregoing oxidation procedure, Albright and Goldman (1,2) described a novel method for the oxidation of alcohols which uses methyl sulfoxide and certain acid anhydrides—e.g., acetic... 

Fortunately, the oxidation of l,2 5,6-di-0-isopropylidene-a-D-glucofura-nose to l,2 5,6-di-0-isopropylidene-a-D-nfoo-hexofuranos-3-ulose (1) can be accomplished using either phosphorus pentoxide (10, 44) or acetic anhydride (10, 52) in methyl sulfoxide although this oxidation is effected with ruthenium tetroxide (6,7, 46), it is exceeding difficult with other oxidizing agents (53). Keto-sugar 1 is reduced stereospecifically... 

The crystalline phenylboronate derived by similar treatment of methyl a-L-fucopyranoside was shown to possess the 3,4-cyclic structure (25). This assignment is based on oxidation of compound 25 with methyl sulfoxide-acetic anhydride and the chromatographic identification of... 

In the case of the condensation of benzyl methyl sulfoxide with bcnzaldchydc (40% yield), the diastereomeric ratio of four enantiomeric (S-sulfinyl alcohols after immediate workup is 41 19 8 32 . 

Addition of Methyl Sulfoxides Reactions with Imines... 

Since these adducts undergo reductive desulfuration with Raney nickel, optically active aryl methyl sulfoxides are versatile reagents for the conversion of imines to optically active amines. 

Metabolites in the degradation of Demeton S-methyl sulfoxide by soil... 

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