The α-effect in benzyl transfers from benzylphenylmethyl sulfonium salts to N-methylbenzohydroxamate anions

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6547-6553

  Fountain, K R ^a   Tad Y, Darlene B ^a   Paul, Timothy W ^a   Golynskiy, Mikhail V ^a  

^a TRUMAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXAMIC ACID DERIVATIVE; SULFONIUM DERIVATIVE;

ARTICLE; ELECTRON TRANSPORT; PKA; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032886037     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981902+     Document Type: Article

References (22)

1. Hoz, S.; Buncel, E. Isr. J. Chem. 1985, 26, 313.
2. Fountain, K. R.; Fountain, D. P.; Michaels, B.; Myers, D. B.; Salmon, J. K.; Van Galen, D. A.; Yu, P. Can. J. Chem. 1990, 69, 798.
3. Fountain, K. R.; Dunkin, T. W.; Patel, K. D. J. Org. Chem. 1997, 62, 3711.
4. Fountain, K. R.; Patel, K. D. J. Org. Chem. 1997, 62, 4795.
5. Andrieux, C. P.; Robert, M.; Saeva, F. D.; Savéant, J.-M. J. Am. Chem. Soc. 1994, 116, 7864.
6. Pross, A. Theoretical and Physical Principles of Organic Reactivity; Wiley-Interscience: New York, 1995; p 177.
7. Kim, W. K.; Ryu, W. S.; Han, I.-S.; Kim, C. K.; Lee, I. J. Phys. Org. 1998, 11, 115.
8. Pross, A.; Shaik, S. J. Am. Chem. Soc. 1982, 47, 3702.
9. N2 Mechanism; John Wiley & Sons: New York, 1992; pp 149-153.
10. Hoz, S. J. Org. Chem. 1982, 47, 3545.
11. Bunnett, J. F. In Techniques of Organic Chemistry, Vol. VIII, Rates and Mechanisms of Reactions; Interscience: New York, 1961; p 191.
12. Fountain, K. R.; Patel, K. D.; Dunkin, T. W.; Powers, J. A.; Van Galen, D. A. J. Org. Chem. 1997, 62, 853.
13. Aubort, J. D.; Hudson, R. F. Chem. Commun. 1970, 1379.
14. (b) Aubort, J. D.; Hudson, R. F. Ibid. 1970, 938.
15. (c) Aubort, J. D.; Hudson, R. F. Ibid. 1970, 1378.
16. Dessolin, M.; Laloi-Diard, M.; Vilas, M. Tetrahedron Lett. 1974, 2405.
17. Um, I.-H.; Yoon, H.-W.; Lee, J.-S.; Moon, H.-J.; Kwon, D.-S. J. Org. Chem. 1997, 62, 5939.
18. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper & Row: Publishers: New York, 1987; p 217.
19. Buncel, E.; Wilson, H.; Chuaqui, C. J. Am. Chem. Soc. 1982, 104, 4896.
20. Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224.
21. Cheng, J.-P.; Liu, B.; Zhang, X.-M. J. Org. Chem. 1998, 63, 7574.
22. Fountain, K. R.; Dunkin, T. W.; Patel, K. D. J. Org. Chem. 1997, 62, 2738.