Rhenium-catalyzed oxidation of sulfides with phenyl sulfoxide

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2260-2261

  Arterburn, Jeffrey B ^a   Nelson, Sherry L ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001625444     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960178x     Document Type: Article

References (15)

1. (a) Madesclaire, M. Tetrahedron 1986, 42, 5459.
2. (b) Drabowicz, J.; Kielbasinski, P.; Mikolajczyk, M. Synthesis of Salphoxides; John Wiley & Sons, Ltd.: New York, 1994; p 109.
3. 2 has been reported: (a) Adam, W.; Mitchell, C. M.; Saha-Moller, C. R. Tetrahedron 1994, 50, 13121. (b) Vassell, K. A ; Espenson, J. H. Inorg. Chem. 1994, 33, 5491.
4. 2 has been reported: (a) Adam, W.; Mitchell, C. M.; Saha-Moller, C. R. Tetrahedron 1994, 50, 13121. (b) Vassell, K. A ; Espenson, J. H. Inorg. Chem. 1994, 33, 5491.
5. (a) Hsu, F. L.; Saafraniec, L. L.; Beaudry, W. T.; Yang, Y. C. J. Org. Chem. 1990, 55, 4153.
6. (b) Miotti, U. J. Chem. Soc., Perkin Trans. 2 1991, 617.
7. Holm, R. H. Chem. Rev. 1987, 87, 1401.
8. Kukushkin, V. Y. Coord. Chem. Rev. 1995, 139, 370.
9. Bryan, J. C.; Stenkamp, R. E.; Tulip, T. H.; Mayer, J. M. Inorg. Chem. 1987, 26, 2283.
10. 4]Cl that has been reported from the reaction of (I) with pyridine. This complex was also not catalytically active for sulfide oxidation.
11. Johnson, N. P.; Lock, C. J. L.; Wilkinson, G. Inorg. Synth. 1967, 9, 145. Trichlorooxobis(triphenylphosphine)rhenium (II) is also commercially available from the Aldrich Chemical Co.
12. 2SO; ΔH = -2.6 kcal/mol. Holm has introduced a thermodynamic scale of oxo transfer reactivity based on the correlation between ΔH values for gas-phase reactions and ΔG values. Holm, R. H.; Donahue, J. P. Polyhedron 1993, 12, 571.
13. The structures of these decomposition products have not yet been identified; however, the fact that no sulfone forms is significant.
14. 3PO); concentration and drying in vacuo gave the corresponding sulfoxides.
15. 2SO/HCl has been reported: Shechter, Y. J. Biol. Chem. 1986, 261, 66.