Dimethyl sulfoxide pivaloyl chloride: A new reagent for oxidation of alcohols to carbonyls

Synthetic Communications

Volumn 38, Issue 5, 2008, Pages 746-753

  Dubey, Abhishek ^a   Kandula, Subba Rao V ^a   Kumar, Pradeep ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Alcohols; Carbonyls; DMSO; Pivaloyl chloride; Swern oxidation

Indexed keywords

ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE; DIMETHYL SULFOXIDE; PIVALIC ACID; REAGENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SWERN OXIDATION;

EID: 39049112839     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701820343     Document Type: Article

References (25)

1. (a) Martin, D.; Hauthal, H. G. Dimethyl Sulfoxide; Halsted Press: New York, 1975;
2. (b) Jacob, S. W.; Rosenbaum, E. E.; Wood, D. C. (eds.) Dimethyl Sulfoxide; vol. 1: Basic Concepts, Dekker: New York, 1971, p. 479.
3. (a) Jacob, S. W.; Rosenbaum, E. E.; Wood, D. C. Basic Concepts of DMSO; Marcel Dekker: New York, 1971;
4. (b) Durst, T. Advances in Organic Chemistry: Methods and Results; Taylor, E. C. and Wynberg, H. Eds.; Interscience: New York, 1969; Vol. 6, p. 285;
5. (c) Epstein, W. W.; Sweat, F. W. Dimethyl sulfoxide oxidation. Chem. Rev. 1967, 67, 247-260;
6. (d) Butterworth, R. F.; Hanessian, S. Selected methods of oxidation in carbohydrate chemistry. Synthesis 1971, 70-88.
7. (a) Sharma, A. K.; Swern, D. Trifluoroacetic anhydride: A new activating reagent for dimethyl sulfoxide in the synthesis of iminosulfuranes. Tetrahedron Lett. 1974, 15, 1503-1506;
8. (b) Huang, S. L.; Omura, K.; Swern, D. Oxidation of sterically hindered alcohols to carbonyls with dimethyl sulfoxide-trifluoroacetic anhydride. J. Org. Chem. 1976, 41, 3329-3331.
9. (a) Omura, K.; Sharma, A. K.; Swern, D. Dimethyl sulfoxide- trifluoroacetic anhydride: A new reagent for oxidation of alcohols to carbonyls. J. Org. Chem. 1976, 41, 957-962;
10. (b) Omura, K.; Swern, D. Oxidation of alcohols by "activated" dimethyl sulfoxide: A preparative, steric and mechanistic study. Tetrahedron 1978, 34, 1651-1660.
11. (a) Mancuso, A. J.; Huang, S. L.; Swern, D. Oxidation of long chains and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chloride. J. Org. Chem. 1978, 43, 2480-2482;
12. (b) Sinaram, B.; Chrisman, W. The effect of different amine bases in the Swern oxidation of β-amino alcohols. Tetrahedron Lett. 1977, 38, 2053-2056.
13. Heintzelman, R. W.; Bailey, R. B.; Swern, D. Sulfoximines, 2: New method for the preparation of N-arylsuloximines. J. Org. Chem. 1976, 41, 2207-2209.
14. 1: Oxidation of secondary alcohols to ketones. J. Org. Chem. 1965, 30, 1107-1110;
15. (b) Albright, J. D.; Goldman, L. Dimthyl sulfoxide-acid anhydride mixture: New reagent for oxidation of alcohols. J. Am. Chem. Soc. 1965, 87, 4214-4216;
16. (c) Albright, J. D.; Goldman, L. Dimethyl sulfoxide-acid anhydride mixture for the oxidation of alcohols. J. Am. Chem. Soc. 1967, 89, 2416-2423.
17. (a) Barton, D. H. R.; Garner, B. J.; Wightman, R. H. A new procedure for the oxidation of alcohols. J. Chem. Soc. 1964, 1855-1857;
18. (b) Takano, S.; Inomata, K.; Tomita, S.; Yanase, M.; Samizu, K.; Ogasawara, K. Oxidation of alcohols using dimethyl sulfoxide and trichloromethyl chloroformate. Tetrahedron Lett. 1988, 29, 6619-6620.
19. Paloma, C.; Cossio, F. P.; Ontoria, J. M.; Odriozola, J. M. Oxidation of alcohols using bis(trichloromethyl) carbonate as activator of dimethyl sulfoxide. J. Org. Chem. 1991, 56, 5948-5951.
20. Luca, L. D.; Giacomelli, G.; Porcheddu, A. A mild and efficient alternative to the classical Swern oxidation. J. Org. Chem. 2001, 66, 7907-7909.
21. Bisai, A.; Chandrasekhar, M.; Singh, V. K. An alternative to the Swern oxidation. Tetrahedron Lett. 2002, 43, 8355-8357.
22. (a) Kandula, S. R. V.; Puranik, V. G.; Kumar, P. 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. 2003, 44, 5015-5017;
23. (b) Fuerstner, A.; Kennedy, J. W. T. Total synthesis of the Tylophora alkaloids Cryptopleurine, (-)-Antofine, (-)-Tylophorine, and (-)- Ficuseptine C. Chem. Eur. J. 2006, 12, 7398-7410;
24. (c) Tiwari, D. K.; Gumaste, V. K.; Deshmukh, A. R. A. S. Azetidin-2,3-dione synthon for stereoselective synthesis of cis- and trans-C-3-alkyl/aryl azetidine-2-ones. Synthesis 2006, 1, 115-122;
25. (d) Chang, C. L.; Kumar, M. P.; Liu, R. S. A highly efficient ruthenuium-catalysed rearragement of α, β-epoxyketone to 1,2-ketone. J. Org. Chem. 2004, 69, 2793-2796.