A non-outer sphere mechanism for the ionization of aryl vinyl sulfides by triarylaminium salts

Journal of the American Chemical Society

Volumn 119, Issue 47, 1997, Pages 11381-11389

  Bauld, Nathan L ^a   Aplin, J Todd ^a   Yueh, Wang ^a   Loinaz, Ainhoa ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ANTIMONY DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFIDE; VINYL DERIVATIVE;

CHEMICAL REACTION; COVALENT BOND; ELECTRON TRANSPORT; IONIZATION; MOLECULAR INTERACTION; REVIEW;

EID: 0031587463     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9706965     Document Type: Review

References (30)

1. Bauld, N. L. Advances in Electron Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich, 1992; Vol. 2, pp 1-66. Bauld, N. L. Tetrahedron 1989, 45, 5307-5363.
2. Bauld, N. L. Advances in Electron Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich, 1992; Vol. 2, pp 1-66. Bauld, N. L. Tetrahedron 1989, 45, 5307-5363.
3. Hubig, S. M.; Bockman, T. M.; Kochi, J. K. J. Am. Chem. Soc. 1996, 118, 3842-3851.
4. Eberson, L.; Olofsson, B.; Svensson, J.-O. Acta Chem. Scand. 1992, 46, 1005-1015.
5. Yueh, W.; Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 1995, 871-873; 1995, 1715-1716.
6. Yueh, W.; Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 1995, 871-873; 1995, 1715-1716.
7. Bauld, N. L.; Aplin, J. T.; Yueh, W.; Endo, S.; Loving, A. J. Phys. Org. Chem. 1997, in press.
8. + correlations.
9. Pabon, R. A.; Bellville, D. J.; Bauld, N. L. J. Am. Chem. Soc. 1983, 105, 5158-5159.
10. Harirchian, B.; Bauld, N. L. Tetahedron Lett. 1987, 28, 927-930.
11. Harirchian, B.; Bauld, N. L. J. Am. Chem. Soc. 1989, 111, 1826-1828.
12. Kim, T.; Pye, R. J.; Bauld, N. L., J. Am. Chem. Soc. 1987, 112, 6285-6290.
13. Reynolds, D. W.; Lorenz, K. T.; Chiou, H.-S.; Bellville, D. J.; Pabon, R. A.; Bauld, N. L. J. Am. Chem. Soc. 1987, 109, 4960.
14. Gassman, P. G.; Singleton, D. A. J. Am. Chem. Soc. 1984, 106, 7993.
15. Baltes, H.; Steckhan, E.; Schäfer, H. J. Chem. Ber. 1978, 111, 1294-1314. The peak potential for cyclopentadiene (vs Ag/AgCl) is given as 1.50 V. The peak potential for phenyl vinyl sulfide is 1.1 V.
16. Yueh, W.; Bauld, N. L. J. Phys. Org. Chem. 1996, 9, 529-538.
17. Shoemaker, D. P.; Garland, C. W.; Nibler, J. W. Experiments in Physical Chemistry; McGraw-Hill: New York, 1989; pp 811-820.
18. McClelland, R. A. Can. J. Chem. 1977, 55, 548-551.
19. Hojo, M.; Masuda, R.; Kamitori, Y.; Okada, E. J. Org. Chem. 1991, 56, 1975-1976.
20. Yueh, W.; Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 1996, 1761-1766.
21. This is a consequence of the formation of neutral 1 as a product of the ionization reaction: Lorenz, K. T.; Bauld, N. L. J. Am. Chem. Soc. 1987, 109, 1157-1160.
22. 17
23. Yueh, W.; Sarker, H.; Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 1995, 1715-1716.
24. Hojo, M.; Masuda, R.; Takagi, S. Synthesis 1978, 4, 284.
25. Bellville, D. J.; Wirth, D. D.; Bauld, N. L. J. Am. Chem. Soc. 1981, 103, 718-720.
26. Kim, T.; Pye, J.; Bauld, N. L. J. Am. Chem. Soc. 1990, 112, 6285.
27. Verboom, W.; Meuer, J.; Brandsma, L. Synthesis 1978, 577.
28. Parham, W. E.; Herberling, J. J. Am. Chem. Soc. 1955, 77, 1175.
29. (a) Parham, W. E.; Stright, P. L. J. Am. Chem. Soc. 1956, 81, 4783.
30. (b) Parham, W. E.; Motter, R. F.; Mayo, G. L. J. Am. Chem. Soc. 1959 81, 3386.