DMSO, DCC

Functionality H2Cr04 acetone CrOs, aq. acetic acid CrOs pyridine NBA r-butanol DMSO DCC Oppenauer DDQ MnOa Pb(0Ac)4 pyridine... 

With DMSO Based Reagents. An alcohol is treated with DMSO, DCC, anhydrous phosphoric acid in what is called Moffatt oxidation. In this way, a primary alcohol can be converted to the aldehyde with no carboxylic acid being produced. 

DMSO, CI3COCOCI / EtjN DMSO, QjCOCOjCCb/EtjN DMSO, DCC, H+ (Pfitzner-Moffatt)... 

Pfltzner and Moffatt report the interesting finding that an equatorial 11 a-hydroxy-steroid is oxidized readily by the DMSO-DCC combination whereas the 11 /3-epimer is inert under the same conditions. The situation is thus the reverse of that found in chromic acid oxidation (Eschenmoser). The authors offer an explanation based on a suggested mechanism for the oxidation. 

Dyer et al. oxidized a furanoside derivative by the DMSO-DCC-pyridinium phosphate method, and Albright and Goldman applied the Pfitzner-Moffatt procedure successfully for oxidation of yohimbine and other indole alkaloids. Suscep-... 

A quite similar method is employed in the one-carbon chain extension of a 5 -phosphonate isostere of pyridoxal 5 -phosphate (Scheme 5.50) The a , 3-O-isopropylideneisopyridoxal is converted into an oc,P-unsaturated phosphonate in yields up to 65% by condensation with sodium tetraethyl methylenediphosphonate. Selective hydrolysis with 10% HCOjH at reflux gives the key diethyl 2-(3-hydroxy-4-hydroxymethyl-2-methyl-5-pyridyl)vinylphosphonate intermediate in 98% yield. After catalytic hydrogenation of the double bond using 5% Pd/C in EtOH, a comparison of methods for the oxidation of the alcohol has been made, including use of MnOi in water, CrO, Py, and DMSO-DCC. Finally, oxidation with activated MnO2 in CHCl, was found to proceed smoothly to give the diethyl 2-(4-formyl-3-hydroxy-2-methyl-5-pyridyl)cthylphosphonate. ... 

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