Dediazoniation of Arenediazonium Ions in Homogeneous Solution. 11. Evidence for Two Intermediates in the Reaction of the 2,4,6-Trimethylbenzenediazonium Ion in 2,2,2-Trifluoroethanol

Journal of the American Chemical Society

Volumn 100, Issue 9, 1978, Pages 2816-2823

  Hashida, Yoji ^a   Landells, Robin G M ^a   Lewis, Graham E ^a   Szele, Ivanka ^a   Zollinger, Heinrich ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001156106     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00477a040     Document Type: Article

References (21)

1. L. Szele and H. Zollinger, J. Am. Chem. Soc., preceding paper in this issue.
2. V. J. Shiner, Jr., W. Dowd, R. D. Fisher, S. R. Hartshorn, M. A. Kessick, L. Milakofsky, and M. W. Rapp, J. Am. Chem. Soc., 91, 4838 (1969).
3. R. G. Bergstrom, R. G. M. Landells, G. H. Wahl, Jr., and H. Zollinger, J. Am. Chem. Soc., 98, 3301 (1976).
4. G. A. Swan and P. Kelly, J. Chem. Soc., 416 (1954).
5. R. Wiebe, V. L. Gaddy, and C. Heins, Jr., ind. Eng. Chem., 24, 823 (1932).
6. E. S. Lewis and R. E. Holliday, J. Am. Chem. Soc., 88, 5043 (1966).
7. D. M. Maharajh and J. Walkley, Nature (London)., 236, 165 (1972).
8. K. R. Brower, J. Am. Chem. Soc., 82, 4535 (1960).
9. J. Miller, “Aromatic Nucleophilic Substitution ”, Elsevier, Amsterdam, 1968, p 29 ff, and references cited therein.
10. H. Zollinger, Acc. Chem. Res., 6, 335 (1973).
11. E. S. Lewis and W. H. Hinds, J. Am. Chem. Soc., 74, 304 (1952).;
12. E. S. Lewis, L. D. Hartung, and B. M. McKay, J. Am. Chem. Soc., 91,419 (1969).
13. P. Burri and H. Zollinger, Heiv. Chim. Acta, 56, 2204 (1973).
14. R. G. Bergstrom, G. H. Wahl, Jr., and H. Zollinger, Tetrahedron Lett., 2975 (1974).
15. R. G. M. Landells, Ph.D. Thesis, University of Edinburqh, 1976.
16. C. G. Swain, J. E. Sheats, and K. G. Harbison, J. Am. Chem. Soc., 97, 783 (1975).
17. C. G. Swain, J. E. Sheats, D. G. Gorenstein, and K. G. Harbison, J. Am. Chem. Soc., 97, 791 (1975).
18. C. G. Swain, J. E. Sheats, and K. G. Harbison, J. Am. Chem. Soc., 97, 796 (1975).
19. H. G. Richey, Jr., and J. M. Richey in “Carbonium Ions ”, Vol. II, G. A. Olah and P. V. R. Schleyer, Ed., Wiley-lnterscience, New York, N.Y., 1970, p 923.
20. J. D. Dill, P. V. R. Schleyer, J. S. Binkley, R. Seeger, J. A. Pople, and E. Haselbach, J. Am. Chem. Soc., 98, 5428 (1976).
21. J. D. Dill, P. V. R. Schleyer, and J. A. Pople, J. Am. Chem. Soc., 99, 1 (1977).