Facile conversion of dithioesters into carboxylic acids or esters using alkaline hydrogen peroxide

Synthesis

Volumn , Issue 21, 2008, Pages 3443-3446

  Grellepois, Fabienne ^a   Portella, Charles ^a  

^a CNRS   (France)

Author keywords

Carboxylic acids; Desulfurization; Esters; Oxidation; Peroxides

Indexed keywords

ACIDS; CARBOXYLIC ACIDS; DESULFURIZATION; ESTERIFICATION; ESTERS; HYDROGEN; HYDROGEN PEROXIDE; ORGANIC ACIDS; ORGANIC COMPOUNDS;

ALKALINE CONDITIONS; DIRECT CONVERSIONS; DITHIOESTERS; ENVIRONMENTALLY FRIENDLY; FACILE CONVERSIONS;

OXIDATION;

CARBOXYLIC ACID; ESTER DERIVATIVE; HYDROGEN PEROXIDE; THIOESTER;

ALKALINITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DESULFURIZATION; OXIDATION;

EID: 56249117676     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083190     Document Type: Article

References (47)

1. For a review on the conversion of C=S into C=O, see: Corsaco, A.; Pistara, V. Tetrahedron 1998, 54, 15027.
2. For reviews on the preparation of dithioesters, see: (a) Ramadas, S. R.; Srinisavan, P. S.; Ramachandran, J.; Sastry, V. V. S. K. Synthesis 1983, 605.
3. (b) Metzner, P.; Thuillier, A. Sulfur Reagents in Organic Synthesis; Academic Press: London, 1994.
4. (c) See also: Abrunhosa, I.; Gulea, M.; Masson, S. Synthesis 2004, 928; and references cited therein.
5. Labiad, B.; Villemin, D. Chem. Ind. (London) 1988, 434.
6. Jorgensen, K. A.; El-Wassimy, M. T. M.; Lawesson, S. O. Tetrahedron 1983, 39, 469.
7. Rees, C. W.; Rakitin, O. A.; Marcos, C. F.; Torroba, T. J. Org. Chem. 1999, 64, 4376.
8. Ito, K.; Nakajima, K. J. Heterocycl. Chem. 1988, 25, 511.
9. Ley, S. V.; Meerholz, C. A.; Barton, D. H. R. Tetrahedron Lett. 1980, 21, 1785.
10. Alper, H.; Kwiatkowska, C.; Petrignani, J. F.; Sibtain, F. Tetrahedron Lett. 1986, 27, 5449.
11. Ishida, M.; Kaga, K.; Sato, H.; Kato, S. Bull. Chem. Soc. Jpn. 1986, 59, 1403.
12. (a) Takahashi, H.; Oshima, K.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1973, 95, 5803.
13. (b) Beslin, P.; Vallée, Y. Tetrahedron 1985, 41, 2691.
14. (c) Meyers, A. I.; Walkup, R. D. Tetrahedron 1985, 41, 5089.
15. (d) Beslin, P.; Perrio, S. Tetrahedron 1991, 47, 6275.
16. (a) Berrada, S.; Desert, S.; Metzner, P. Tetrahedron 1988, 44, 3575.
17. (b) Kpegba, K.; Metzner, P.; Rakotonirina, R. Tetrahedron 1989, 45, 2041.
18. (c) Jung, M. F.; Parker, M. H. J. Org. Chem. 1997, 62, 7094.
19. (d) Sibi, M. P.; Rheault, T. R.; Chandramouli, S. V.; Jasperse, C. P. J. Am. Chem. Soc. 2002, 124, 2924.
20. (e) Satoh, T.; Miura, M.; Sakai, K.; Yokoyama, Y. Tetrahedron 2006, 62, 4253.
21. (f) Spivey, A. C.; Martin, L. J.; Grainger, D. M.; Ortner, J.; White, A. J. P. Org. Lett. 2006, 8, 3891.
22. Derwing, C.; Frank, H.; Hoppe, D. Eur. J. Org. Chem. 1999, 3519.
23. El-Wassimy, M. T. M.; Jorgensen, K. A.; Lawesson, S. O. Chem. Scr. 1984, 24, 80.
24. Grellepois, F.; Timoshenko, V. M.; Shermolovich, Y. G.; Portella, C. Org. Lett. 2006, 8, 4323.
25. 3 carboxylic acids, see for example: Hiyama, T. Organofluorine Compounds: Chemistry and Applications; Springer Verlag: Berlin, 2000.
26. (a) Strukul, G. Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Kluwer Academic: Dordrecht, 1992.
27. (b) Burke, S. D.; Danheiser, R. L. Handbook of Reagents for Organic Synthesis: Oxidizing and Reducing Agents; Wiley: Chichester, 1999, 174-178.
28. For the oxidation of thiols into disulfides with alkaline hydrogen peroxide, see: (a) Price, C. C.; Stacy, G. W. Org. Synth., Coll. Vol. III; John Wiley & Sons: London, 1955, 86.
29. (b) Pascal, I.; Tarbell, D. S. J. Am. Chem. Soc. 1957, 79, 6015.
30. (c) Hesse, J. E.; Truby, F. K. Chem. Ind. (London) 1965, 680.
31. Aqueous hydrogen peroxide could be replaced by solid urea-hydrogen peroxide adduct (UHP). Under these conditions, acid 4 was isolated in 88% yield.
32. R, MS peaks) with those of authentic samples of dithioester 3, acid 4, ester 5, thiolester 6, thionoester 7, sulfine 8, and dibenzyl disulfide.
33. For a study of the mechanism of the conversion of thioamides into amides with hydrogen peroxide at various pH see: Cashman, J. R.; Hanzlik, R. P. J. Org. Chem. 1982, 47, 4645.
34. Zwanenburg, B.; Thys, L.; Strating, J. Tetrahedron Lett. 1967, 8, 3453.
35. Oxathiiranes have already been postulated as intermediates for the rearrangement of dithioesters into dithioperoxyesters, see: Metzner, P.; Pham, T. N. J. Chem. Soc., Chem. Commun. 1988, 390.
36. Snyder, J. P. J. Am. Chem. Soc. 1974, 96, 5005.
37. Hu, N. X.; Aso, Y.; Otsubo, T.; Ogura, F. Tetrahedron Lett. 1986, 27, 6099.
38. Mohammadpoor-Baltork, I.; Memarian, H. R.; Bahrami, K. Monatsh. Chem. 2004, 135, 411.
39. Pirkle, W. H.; Sowin, T. J. J. Org. Chem. 1987, 52, 3011.
40. Narasimhamurthy, N.; Samuelson, A. G. Tetrahedron Lett. 1986, 27, 3911.
41. El-Wassimy, M. T. M.; Jorgensen, K. A.; Lawesson, S. O. Tetrahedron 1983, 39, 1729.
42. Lemarie, M.; Pham, T. N.; Metzner, P. Tetrahedron Lett. 1991, 32, 7411.
43. Mohammadpoor-Baltork, I.; Sadeghi, M. M.; Esmayilpour, K. Synth. Commun. 2003, 33, 953.
44. Despite the fact that only 1 equiv of base is required, using a larger amount reduced the reaction time (1 h instead of 15 h).
45. Aqueous hydrogen peroxide could be replaced by solid urea-hydrogen peroxide adduct (UHP). Under these conditions, ester 5 was isolated in 50% yield.
46. (a) Cazes, B.; Julia, S. Tetrahedron Lett. 1978, 19, 4065.
47. (b) Metzner, P.; Thuillier, A. Sulfur Reagents in Organic Synthesis; Academic Press: London, 1994, 41.