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Swern oxidation From Wikipedia, the free encyclopedia The Swern oxidation , named after Daniel Swern , is a chemical reaction whereby a primary or secondary alcohol is oxidized to an aldehyde or ketone using oxalyl chloride , dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine . [1][2][3] The reaction is known for its mild character and wide tolerance of functional groups . [4][5][6][7] The by-products are dimethyl sulfide (Me 2 S), carbon monoxide (CO), carbon dioxide (CO 2 ) and when triethylamine is used as base triethylammonium chloride (Et 3 NHCl). Of the volatile by-products, dimethyl sulfide has a strong, pervasive odor and carbon monoxide is acutely toxic, so the reaction and the work-up needs to be performed in a fume hood. Dimethyl sulfide is a volatile liquid (B.P. 37 °C) with an unpleasant odour at high concentrations. [8][9][10] Mechanism[] The first step of the Swern oxidation is the low-temperature reaction of dimethyl sulfoxide (DMSO), 1a , formally as resonance contributor 1b , with oxalyl chloride , 2 . The first intermediate, 3 , quickly decomposes giving off CO 2 and CO and producing chloro(dimethyl)sulfonium chloride, 4 . After addition of the alcohol 5 , the chloro(dimethyl)sulfonium chloride 4 reacts with the alcohol to give the key alkoxysulfonium ion intermediate, 6 . The addition of at least 2 equivalents of base typically
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  • Winter '08
  • AUE
  • Swern oxidation, Daniel Swern

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