Ei elimination: An unprecedented facet of sulfone chemistry

Journal of the American Chemical Society

Volumn 122, Issue 20, 2000, Pages 4968-4971

  Cubbage, Jerry W ^a   Vos, Brian W ^a   Jenks, William S ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; STYRENE; SULFONE DERIVATIVE;

ARTICLE; ENTHALPY; GAS; REACTION ANALYSIS; THERMODYNAMICS;

EID: 0034709425     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994150p     Document Type: Article

References (37)

1. Kice, J. L. Desulfonylation Reactions; Kharasch, N., Meyers, C. Y., Eds.; Pergamon Press: Oxford, 1966; pp 115-136.
2. Vögtle, F.; Rossa, L. Angew. Chem., Int. Ed. Engl. 1979, 18, 515-529.
3. Martin, G. Pyrolysis of Organosulphur Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons, Ltd.: New York, 1993; pp 395-437.
4. Woodward, R. B.; Hoffman, R. The Conservation of Orbital Symmetry; VCH Publishers: Weinheim, 1970.
5. Block, E. J. Am. Chem. Soc. 1972, 94, 642-644.
6. Block, E. J. Am. Chem. Soc. 1972, 94, 644-645.
7. Block, E.; Weidman, S. W. J. Am. Chem. Soc. 1973, 95, 5046-8.
8. Block, E.; O'Connor, J. J. Am. Chem. Soc. 1974, 96, 3929-44.
9. Orbital considerations preclude a true pericyclic reaction.
10. Bordwell, F. G.; Happer, D. A. R.; Cooper, G. D. Tetrahedron Lett. 1972, 2759-2762.
11. Redman, R. P.; Thomas, P. J.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 2 1978, 1135-1144.
12. Marshall, D. R.; Thomas, P. J.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 2 1977, 1914-1919.
13. Hoffman, J. E.; Wallace, T. J.; Schriesheim, A. J. Am. Chem. Soc. 1964, 86, 1561-1563.
14. Marshall, D. R.; Thomas, P. J.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 2 1977, 1898-1909.
15. Thomas, P. J.; Stirling, C. J. M. J. Chem. Soc., Chem. Commun. 1976, 829-830.
16. Buncel, E.; Decouzon, M.; Formento, A.; Gal, J.-F.; Herreros, M.; Li, L.; Maria, P.-C.; Koppel, I.; Kurg, R. J. Am. Soc. Mass Spectrom. 1997, 8, 262-269.
17. Baldwin, A. C.; Davidson, I. M. T.; Howard, A. V. J. Chem. Soc. 1975, 71, 972-979.
18. Cubbage, J. W.; Guo, Y.; Jenks, W. S. To be submitted for publication.
19. Melander, L.; Saunders, W., Jr. Reaction Rates of Isotopic Molecules; Wiley: New York, 1980.
20. Anisimov, V.; Paneth, P. J. Math. Chem. 1999, 26, 75-86.
21. Paneth, P. Comput. Chem. 1995, 19, 231-240.
22. Bigeleisen, J.; Mayer, M. G. J. Chem. Phys. 1947, 15, 261-267.
23. Wolfsburg, M. Acc. Chem. Res. 1972, 6, 225-233.
24. Melander, L. Isotope Effects on Reaction Rates; Ronald Press: New York, 1960.
25. Benson, S. W. Chem. Rev. 1978, 78, 23-35.
26. Herron, J. Thermochemistry of Sulfoxides and Sulfones; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley and Sons Ltd.: New York, 1988; pp 95-105.
27. Entwilstle, I. K.; Johnstone, R. A. W.; Millard, B. J. J. Chem. Soc. C 1967, 302-306.
28. Oda, R.; Yamamoto, K. J. Org. Chem. 1961, 26, 4679-4681.
29. Russell, G. A.; Sabourin, E.; Mikol, G. J. J. Org. Chem. 1966, 31, 4-2858.
30. Guo, Y. Study on the Photolysis and Thermolysis of Alkyl Aryl Sulfoxides; Iowa State University: Ames, IA, 1997.
31. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, N.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347-1363.
32. Bode, B. M.; Gordon, M. S. J. Mol. Graphics Mod. 1998, 16, 133-138.
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stevanov, B.; Nanayakkara, A.; Callacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision D.1; Gaussian, Inc.: Pittsburgh, PA, 1995.
34. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639-5648.
35. Stein, S. E.; Lias, S. G.; Liebman, J. F.; Levin, R. D.; Kafafi, S. A. NIST Structures and Properties: NIST Standard Reference Database 25, 2.0 ed.; U.S. Department of Commerce, NIST: Gaithersburg, MD, 1994.
36. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221-7230.
37. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063-1079.