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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 5
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Original Articles

Dimethyl Sulfoxide Pivaloyl Chloride: A New Reagent for Oxidation of Alcohols to Carbonyls

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Pages 746-753 | Received 10 Sep 2007, Published online: 15 Feb 2008

References

  • Martin , D. and Hauthal , H. G. 1975 . Dimethyl Sulfoxide New York : Halsted Press .
  • Jacob , S. W. , Rosenbaum , E. E. and Wood , D. C. 1971 . Dimethyl Sulfoxide Vol. 1 , 479 New York : Basic Concepts, Dekker .
  • Jacob , S. W. , Rosenbaum , E. E. and Wood , D. C. 1971 . Basic Concepts of DMSO New York : Marcel Dekker .
  • Durst , T. 1969 . Advances in Organic Chemistry: Methods and Results Edited by: Taylor , E. C. and Wynberg , H. Vol. 6 , 285 New York : Interscience .
  • Epstein , W. W. and Sweat , F. W. 1967 . Dimethyl sulfoxide oxidation . Chem. Rev. , 67 : 247 – 260 .
  • Butterworth , R. F. and Hanessian , S. 1971 . Selected methods of oxidation in carbohydrate chemistry . Synthesis , : 70 – 88 .
  • Sharma , A. K. and Swern , D. 1974 . Trifluoroacetic anhydride: A new activating reagent for dimethyl sulfoxide in the synthesis of iminosulfuranes . Tetrahedron Lett. , 15 : 1503 – 1506 .
  • Huang , S. L. , Omura , K. and Swern , D. 1976 . Oxidation of sterically hindered alcohols to carbonyls with dimethyl sulfoxide‐trifluoroacetic anhydride . J. Org. Chem. , 41 : 3329 – 3331 .
  • Omura , K. , Sharma , A. K. and Swern , D. 1976 . Dimethyl sulfoxide‐trifluoroacetic anhydride: A new reagent for oxidation of alcohols to carbonyls . J. Org. Chem. , 41 : 957 – 962 .
  • Omura , K. and Swern , D. 1978 . Oxidation of alcohols by “activated” dimethyl sulfoxide: A preparative, steric and mechanistic study . Tetrahedron , 34 : 1651 – 1660 .
  • Mancuso , A. J. , Huang , S. L. and Swern , D. 1978 . Oxidation of long chains and related alcohols to carbonyls by dimethyl sulfoxide “activated” by oxalyl chloride . J. Org. Chem. , 43 : 2480 – 2482 .
  • Sinaram , B. and Chrisman , W. 1977 . The effect of different amine bases in the Swern oxidation of β‐amino alcohols . Tetrahedron Lett. , 38 : 2053 – 2056 .
  • Heintzelman , R. W. , Bailey , R. B. and Swern , D. 1976 . Sulfoximines, 2: New method for the preparation of N‐arylsuloximines . J. Org. Chem. , 41 : 2207 – 2209 .
  • Albright , J. D. and Goldman , L. 1965 . Indole alkaloids, III1: Oxidation of secondary alcohols to ketones . J. Org. Chem. , 30 : 1107 – 1110 .
  • Albright , J. D. and Goldman , L. 1965 . Dimthyl sulfoxide‐acid anhydride mixture: New reagent for oxidation of alcohols . J. Am. Chem. Soc. , 87 : 4214 – 4216 .
  • Albright , J. D. and Goldman , L. 1967 . Dimethyl sulfoxide–acid anhydride mixture for the oxidation of alcohols . J. Am. Chem. Soc. , 89 : 2416 – 2423 .
  • Barton , D. H. R. , Garner , B. J. and Wightman , R. H. 1964 . A new procedure for the oxidation of alcohols . J. Chem. Soc. , : 1855 – 1857 .
  • Takano , S. , Inomata , K. , Tomita , S. , Yanase , M. , Samizu , K. and Ogasawara , K. 1988 . Oxidation of alcohols using dimethyl sulfoxide and trichloromethyl chloroformate . Tetrahedron Lett. , 29 : 6619 – 6620 .
  • Paloma , C. , Cossio , F. P. , Ontoria , J. M. and Odriozola , J. M. 1991 . Oxidation of alcohols using bis(trichloromethyl) carbonate as activator of dimethyl sulfoxide . J. Org. Chem. , 56 : 5948 – 5951 .
  • Luca , L. D. , Giacomelli , G. and Porcheddu , A. 2001 . A mild and efficient alternative to the classical Swern oxidation . J. Org. Chem. , 66 : 7907 – 7909 .
  • Bisai , A. , Chandrasekhar , M. and Singh , V. K. 2002 . An alternative to the Swern oxidation . Tetrahedron Lett. , 43 : 8355 – 8357 .
  • Kandula , S. R. V. , Puranik , V. G. and Kumar , P. 2003 . Synthesis of novel chiral spirodione, (6R,7R)‐7‐phenyl‐1‐oxaspiro[5,5]undec‐3‐ene‐2,5‐dione: Application to the asymmetric Diels–Alders reaction with high π‐facial selectivity . Tetrahedron Lett. , 44 : 5015 – 5017 .
  • Fuerstner , A. and Kennedy , J. W. T. 2006 . Total synthesis of the Tylophora alkaloids Cryptopleurine, (–)‐Antofine, (–)‐Tylophorine, and (–)‐ Ficuseptine C . Chem. Eur. J. , 12 : 7398 – 7410 .
  • Tiwari , D. K. , Gumaste , V. K. and Deshmukh , A. R. A. S. 2006 . Azetidin‐2,3‐dione synthon for stereoselective synthesis of cis‐ and trans‐C‐3‐alkyl/aryl azetidine‐2‐ones . Synthesis , 1 : 115 – 122 .
  • Chang , C. L. , Kumar , M. P. and Liu , R. S. 2004 . A highly efficient ruthenuium‐catalysed rearragement of α,β‐epoxyketone to 1,2‐ketone . J. Org. Chem. , 69 : 2793 – 2796 .

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