Binuclear manganese complexes as catalysts in the selective and efficient oxidation of sulfides to sulfones

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7055-7058

  Barton, Derek H R ^a   Li, Wenge ^a   Smith, Jason A ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MANGANESE DERIVATIVE; SULFIDE; SULFONE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; OXIDATION;

EID: 0032563844     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01518-4     Document Type: Article

References (11)

1. 1. Simpkins, S. Sulfones in Organic Synthesis; Permagon Press: Oxford, 1993; Page, P. Organosulfur Chemistry: Synthetic Aspects; Academic Press: New York, 1995.
2. 1. Simpkins, S. Sulfones in Organic Synthesis; Permagon Press: Oxford, 1993; Page, P. Organosulfur Chemistry: Synthetic Aspects; Academic Press: New York, 1995.
3. 2. Patai, S. and Rappoport, Z. Syntheses of Sulfones, Sulfoxides and Cyclic Sulfides; John Wiley & sons: Chichester, 1994.
4. 3. Rozen, S.; Bareket, Y. J. Org. Chem. 1997, 62, 1457-1462.
5. 4 Barton, D.H.R.; Choi, S-Y.; Hu, B.; Smith J.A. Tetrahedron 1998, 54, 3367.
6. 5. a) Wieghardt, K.; Bossek, U.; Nuber, B.; Weiss, J.; Bonvoisin, J.; Corbella, M.; Vitols, S.E.; Girerd, J.J. J. Am. Chem. Soc. 1988, 110, 7398-7411.
7. b) Hage, R.; Iburg, J.E.; Kerschner, J.; Koek, J.H.; Lempers, E.L.M.; Martens, R.J.; Racherla, U.S.; Russel, S.W.; Swarthoff, T.; van Vliet, M.R.P.; Warnaar, J.B.; van der Wolf, L.; Krijnen, B. Nature 1994, 369, 637-639;
8. 6. Typical reaction conditions for sulfide oxidation: n-Dibutyl sulfide (2mmol) was dissolved in pyridine (10ml) at room temperature. The catalyst 1 was added (30mg, ∼1.8mol%) followed by periodic acid (4mmol) and the reaction mixture stirred rapidly. A complex of iodic acid/ pyridine slowly forms as the reaction progresses. Reaction times and product distribution were monitored by GC analysis for volatile compounds. Yields for other derivatives were detemined by isolation of the product.
9. 7. Turnover numbers for the catalyst were ∼600.
10. 8. Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272-7276.
11. 9. Zondervan, C.; Hage, R.; Ferringa, B.L. J. Chem. Soc., Chem. Commun. 1997, 419-420.