Dimethyl sulfoxide-phosphorus pentaoxide

Selective oxidation of amylose at C3 has been achieved with dimethyl sulfoxide/phosphorus pentaoxide [119]. In contrast, the oxidation of unprotected cellulose with dimethyl sulfox-ide/acetic anhydride [120] or dicyclohexylcarbodiimide/dimethyl sulfoxide [121] produced a product containing modified 8-D-glucopyranosyl units - some with a carbonyl function at C2, some with a carbonyl function at C3, and some with carbonyl functions at both C2 and C3[122],... 

SAFETY PROFILE A corrosive irritant to skin, eyes, and mucous membranes. Questionable carcinogen with experimental tumorigenic data. Can explode with Pb02. Will react with water or steam to produce heat and toxic and corrosive fumes. Incompatible with alkalies, diethyl ether, dimethyl sulfoxide, dinitrogen pentaoxide, lead dioxide, phosphorus. When heated to decomposition it emits highly toxic fumes of Cr and SOx. See also SULFURIC ACID and HYDROCHLORIC ACID, which are formed upon hydrolysis. 

Onodera, K., Hirano, S., Kashimura, N. Oxidation of carbohydrates with dimethyl sulfoxide containing phosphorus pentaoxide. J. Am. 

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