215F07-notes-9-17-07 - Chem 215 F07 Notes Dr Masato Koreeda...

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Chem 215 F07 Notes – Dr. Masato Koreeda - Page 1 of 3. Date: September 17, 2007 Chapter 13. Alcohols, Diols, and Ethers (continued) VI-2. Non chromium-based Oxidation Reactions: “greener” methods i) Swern oxidation : • usually using dichloromethane (CH 2 Cl 2 ) as the solvent anhydrous (i.e., no water present!), non-acidic conditions • 1°-alcohol: stops at an aldehyde; 2°-alcohol: gives a ketone R C O H H H H 3 C S CH 3 O dimethyl sulfoxide oxalyl chloride 1. N(CH 2 CH 3 ) 3 2. triethylamine R C O H Mechanism: H 3 C S CH 3 O Cl C C Cl O O Cl C C Cl O O H 3 C S CH 3 O Cl C C Cl O O H 3 C S CH 3 O C C Cl O O Cl Cl S CH 3 CH 3 Cl CO 2 , CO, Cl O C R H H H O C R H H S CH 3 H 3 C H O C R H H S C H 3 C B H BH H H H N(CH 2 CH 3 ) 3 This is the species in the solution after step 1. O C R H H S C H 3 C H H HN(CH 2 CH 3 ) 3 highly acidic Hs! pK a ~ 12-13 O C H R H 3 C S C H H H + Oxidation step! "intramolecular process" Note: O H D O H 3 C S CH 2 D H 3 C S CH 3 O 1.
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  • Fall '07
  • Koreeda
  • Reaction, H3C, H3C Cl, O H R C H O H H3C Cl C C O O S

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