Synthesis, enantiomeric conformations, and stereodynamics of aromatic orffto-substituted disulfones

Organic Letters

Volumn 3, Issue 9, 2001, Pages 1407-1410

  Lacour, Jérôme ^a   Monchaud, David ^a   Bernardinelli, Gérald ^a   Favarger, France ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000953640     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015804d     Document Type: Article

References (22)

1. Hellwinkel, D.; Wilfinger, H. J. Chem. Ber. 1970, 103, 1056-1064. Allcock, H. R.; Bissell, E. C. J. Am. Chem. Soc. 1973, 95, 3154-3157. Hellwinkel, D.; Krapp, W. Phosphorus 1976, 6, 91-93. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1976, 955-958. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1979, 40-44. Cavezzan, J.; Etemad-Moghadam, G.; Koenig, M.; Klaebe, A. Tetrahedron Lett. 1979, 795-798. Lacour, J.; Ginglinger, C.; Grivet, C.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 608-609.
2. Hellwinkel, D.; Wilfinger, H. J. Chem. Ber. 1970, 103, 1056-1064. Allcock, H. R.; Bissell, E. C. J. Am. Chem. Soc. 1973, 95, 3154-3157. Hellwinkel, D.; Krapp, W. Phosphorus 1976, 6, 91-93. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1976, 955-958. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1979, 40-44. Cavezzan, J.; Etemad-Moghadam, G.; Koenig, M.; Klaebe, A. Tetrahedron Lett. 1979, 795-798. Lacour, J.; Ginglinger, C.; Grivet, C.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 608-609.
3. Hellwinkel, D.; Wilfinger, H. J. Chem. Ber. 1970, 103, 1056-1064. Allcock, H. R.; Bissell, E. C. J. Am. Chem. Soc. 1973, 95, 3154-3157. Hellwinkel, D.; Krapp, W. Phosphorus 1976, 6, 91-93. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1976, 955-958. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1979, 40-44. Cavezzan, J.; Etemad-Moghadam, G.; Koenig, M.; Klaebe, A. Tetrahedron Lett. 1979, 795-798. Lacour, J.; Ginglinger, C.; Grivet, C.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 608-609.
4. Hellwinkel, D.; Wilfinger, H. J. Chem. Ber. 1970, 103, 1056-1064. Allcock, H. R.; Bissell, E. C. J. Am. Chem. Soc. 1973, 95, 3154-3157. Hellwinkel, D.; Krapp, W. Phosphorus 1976, 6, 91-93. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1976, 955-958. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1979, 40-44. Cavezzan, J.; Etemad-Moghadam, G.; Koenig, M.; Klaebe, A. Tetrahedron Lett. 1979, 795-798. Lacour, J.; Ginglinger, C.; Grivet, C.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 608-609.
5. Hellwinkel, D.; Wilfinger, H. J. Chem. Ber. 1970, 103, 1056-1064. Allcock, H. R.; Bissell, E. C. J. Am. Chem. Soc. 1973, 95, 3154-3157. Hellwinkel, D.; Krapp, W. Phosphorus 1976, 6, 91-93. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1976, 955-958. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1979, 40-44. Cavezzan, J.; Etemad-Moghadam, G.; Koenig, M.; Klaebe, A. Tetrahedron Lett. 1979, 795-798. Lacour, J.; Ginglinger, C.; Grivet, C.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 608-609.
6. Hellwinkel, D.; Wilfinger, H. J. Chem. Ber. 1970, 103, 1056-1064. Allcock, H. R.; Bissell, E. C. J. Am. Chem. Soc. 1973, 95, 3154-3157. Hellwinkel, D.; Krapp, W. Phosphorus 1976, 6, 91-93. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1976, 955-958. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1979, 40-44. Cavezzan, J.; Etemad-Moghadam, G.; Koenig, M.; Klaebe, A. Tetrahedron Lett. 1979, 795-798. Lacour, J.; Ginglinger, C.; Grivet, C.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 608-609.
7. Hellwinkel, D.; Wilfinger, H. J. Chem. Ber. 1970, 103, 1056-1064. Allcock, H. R.; Bissell, E. C. J. Am. Chem. Soc. 1973, 95, 3154-3157. Hellwinkel, D.; Krapp, W. Phosphorus 1976, 6, 91-93. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1976, 955-958. Koenig, M.; Klaebe, A.; Munoz, A.; Wolf, R. J. Chem. Soc., Perkin Trans. 2 1979, 40-44. Cavezzan, J.; Etemad-Moghadam, G.; Koenig, M.; Klaebe, A. Tetrahedron Lett. 1979, 795-798. Lacour, J.; Ginglinger, C.; Grivet, C.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 608-609.
8. See Lacour et al. (last reference of footnote 1) and the following: Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 2379-2380. Lacour, J.; Goujon-Ginglinger, C.; Torche-Haldimann, S.; Jodry, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695-3697. Ratni, H.; Jodry, J. J.; Lacour, J.; Kündig, E. P. Organometallics 2000, 19, 3997-3999.
9. See Lacour et al. (last reference of footnote 1) and the following: Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 2379-2380. Lacour, J.; Goujon-Ginglinger, C.; Torche-Haldimann, S.; Jodry, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695-3697. Ratni, H.; Jodry, J. J.; Lacour, J.; Kündig, E. P. Organometallics 2000, 19, 3997-3999.
10. See Lacour et al. (last reference of footnote 1) and the following: Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 2379-2380. Lacour, J.; Goujon-Ginglinger, C.; Torche-Haldimann, S.; Jodry, J. J. Angew. Chem., Int. Ed. 2000, 39, 3695-3697. Ratni, H.; Jodry, J. J.; Lacour, J.; Kündig, E. P. Organometallics 2000, 19, 3997-3999.
11. For a general overview of atropisomerism, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 1142-1155.
12. Suzuki, H.; Nakamura, K.; Goto, R. Bull. Chem. Soc. Jpn. 1966, 39, 128-131.
13. Suzuki, H.; Abe, H. Tetrahedron Lett. 1995, 36, 6239-6242.
14. Lacour, J.; Barchéchath, S.; Jodry, J. J.; Ginglinger, C. Tetrahedron Lett. 1998, 39, 567-570.
15. Corey, E. J.; Bailar, J. C., Jr. J. Am. Chem. Soc. 1959, 81, 2620-2629.
16. Von Zelewsky, A. Stereochemistry of Coordination Compounds; John Wiley & Sons: Chichester, U.K., 1996.
17. For an example of such chiral conformation in a highly twisted hexasubstituted arene, see: Collard, D. M.; Sadri, M. J.; VanDerveer, D.; Hagen, K. S. J. Chem. Soc., Chem. Commun. 1995, 1357-8.
18. See the CIF file in the Supporting Information.
19. Salt 7 was prepared following the directions found in Krauthausen, E. In Organosulfur Compounds; fourth ed.; Klamann, D., Ed.; Georg Thieme Verlag: Stuttgart, 1985; Vol. E11, p 619.
20. No attempts have been made to determine which of the two diastereomeric conformations is preferred.
21. c/Δv)) was used to determine the activation energy, ΔC‡, from the coalescence temperature, Tc (K), and the frequency separation of the peaks, Av (Hz).
22. c ≥ 147°C and a minimum Av value of 29 Hz (Δδ -77.35 to -77.53).