The reactivity-selectivity principle and the electrophilic substitution of aromatic compounds

Tetrahedron Letters

Volumn 38, Issue 44, 1997, Pages 7649-7652

  White, Emil H ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BENZENE DERIVATIVE; BENZYL DERIVATIVE; NITROSAMINE; TOLUENE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; MOLECULAR INTERACTION; STEREOCHEMISTRY;

EID: 0030714969     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10083-1     Document Type: Article

References (23)

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2. (b) Johnson, C. D. Chem. Rev. 1975, 75, 755-765.
3. (c) Arnett, E. M.; Reich R. J. Am. Chem. Soc. 1980, 102, 5892-5902.
4. (a) Pross, A. Advances in Physical Organic Chemistry 1977,14, 69-132.
5. (b) Jencks, W. P. Chem. Rev. 1985, 85, 511-527.
6. (c) Buncel, E.; Wilson, H. J. Chem. Ed. 1987, 64, 475-480.
7. Johnson, C. D.; Schofield, K. J. Am. Chem. Soc. 1973, 95, 270-272.
8. Johnson, C. D. "The Hammett Equation," The University Press, Cambridge, 1973; p. 187.
9. (a) Olah, G. A., Ed., Friedel-Crafts and Related Reactions; Vols. 1-4, Wiley: New York, 1963-1965.
10. (b) Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; 3rd ed., Harper and Row: New York, 1987; p. 626.
11. Ref. 2c, and ref. 4 cited therein.
12. (a) Olah, G. A.; Kuhn, S. J.; Flood, S. H. J. Am. Chem. Soc. 1962, 84, 1688-1695.
13. (b) Olah, G. A. Accts. Chem. Res. 1971, 4, 240-248.
14. (c) Olah, G. A.; Kobayashi, S.; Tashiro, M. J. Am. Chem. Soc. 1972, 94, 7448-7461.
15. Stock, L. M.; Brown, H. C. Adv. in Phys. Org. Chem. 1963, 1, 35-154, and cited references to J. Am. Chem. Soc. 1953, 1956, and 1959.
16. Stock, L. M.; Brown, H. C. Adv. in Phys. Org. Chem. 1963, 1, 35-154, and cited references to J. Am. Chem. Soc. 1953, 1956, and 1959.
17. 3,4
18. 1a "Qualitatively, the principle means therefore that log k-log K relationships such as embodied in the Hammett or Brønsted treatments of data will be curved, approaching a zero slope as k becomes larger; in the limit, zero selectivity as denoted by zero slopes (ρ, α or ß) of such plots is produced by reagents of infinite reactivity, coincident with diffusion control."
19. White, E. H.; Darbeau, R. W.; Darbeau, N. R.; Chen, Y.; Chen S.; Chen, D. J. Org. Chem. 1996, 61(23), 7986-7987.
20. Similar values were measured for reaction solutions diluted with chloroform.
21. 7,8 are intermediates in the standard Friedel-Crafts alkylation.
22. 11
23. benzene/6 (OCH3) has not been made.