Oxidation_2011_rev

Oxidation_2011_rev - General Summary of Oxidative Function Group Interconversions OH O O R R(H alcohols Dimethylsulfoxide-Mediated Oxidations

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Dimethylsulfoxide-Mediated Oxidations Mancuso, Swern, Synthesis 1981 , 165 Tidwell, Synthesis 1990 , 857 Dess-Martin Periodinane (DMP) Dess, Martin, J. Org. Chem. 1983 , 4155 Schrieber, J. Org. Chem. 1994 , 7549 o -Iodoxybenzoic Acid (IBX) Santagostino, J. Org. Chem. 1999 , 4537 tetra- n -Propylammonium Perruthenate (TPAP) Ley, Synthesis 1994 , 639 N -Oxoammonium-Mediated Oxidation Sheldon Adv. Syn. Cat. 2001 , 1051 Manganese Dioxide (if allylic or benzylic) Fatiadi, Synthesis 1976 , 65 Fatiadi, J. Synthesis 1976 , 133 Barium Manganate Fatiadi, J. Synthesis 1987 , 85-127 alcohols aldehydes or ketones R R'(H) OH R R'(H) O aldehydes carboxylic acids Sodium Chlorite Roth, J. Org. Chem. 1980 , 4825 Postassium Permanganate Fatiadi, Synthesis 1987 , 85 Pyridinium Dichromate/DMF/H 2 O Corey, Tetrahedron Lett. 1979 , 399 Jones Oxidation Org. Syn . 1973 , coll. vol. 5 , 310 R H O R OH O Collins' Reagent (CrO 3 /pyr) Collins, Org. Synth. 1972 , 52 , 5 Pyridinium Chlorochromate (PCC) Corey, Tetrahedron Lett. 1975 , 2647 Pyridinium Dichromate (PDC) Corey, Tetrahedron Lett. 1979 , 399 Sodium Hypochlorite Albizati, Tetrahedron Lett. 1982 , 4647 selective for 2° over 1° N -Bromosuccinimide Corey, Tetrahedron Lett. 1979 , 2745 selective for 2° over 1° Cerium (IV) Oxidants Nozaki, H. Tetrahedron Lett. 1982 , 539 Oppenauer Oxidation Huskens, J. Synthesis 1994 , 1007 Tsuji Oxidation Tsuji, Tetrahedron 1987 , 3903 Fetizon's Reagent Fetizon, Tetrahedron Lett. 1972 , 4445 General Summary of Oxidative Function Group Interconversions: 1° alcohols carboxylic acids R OH R OH O Ruthenium Tetroxide Sharpless,
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This note was uploaded on 01/03/2012 for the course CH 242a taught by Professor List during the Fall '10 term at Caltech.

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Oxidation_2011_rev - General Summary of Oxidative Function Group Interconversions OH O O R R(H alcohols Dimethylsulfoxide-Mediated Oxidations

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