[9,9]-Sigmatropic Shift in a Benzidine-Type Rearrangement

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3794-3795

  Park, Koon Ha ^a   Kang, Jin Soo ^a  

^a Chungnam National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343747572     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9703966     Document Type: Article

References (24)

1. (a) Park, K. H. Heavy-Atom Kinetic Isotope Effects in Solving Mechanisms of Benzidine Rearrangements: Hydrazobenzene and 2,2′-Dimethoxyhydrazobenzene. Ph.D. Dissertation, Texas Tech University, 1983.
2. (b) Dewar, M. J. S. In Molecular Rearrangements; de Mayo, P., Ed.; Interscience: New York, 1969; Vol. 1, pp 323-343.
3. (c) Shine, H. J. In Mechanisms of Molecular Migrations; Thyagarajan, B. S., Ed.; Interscience: New York, 1969; Vol. 2, pp 191-247.
4. (d) Shine, H. J. In Aromatic Rearrangements; Elsevier: New York, 1967; pp 126-179.
5. (e) Cox, R. A.; Buncel, E. In The Chemistry of the Hydrazo, Azo, and Azoxy Groups; Patai, S., Ed.; Wiley: New York, 1975; pp 775-859.
6. (f) Banthorpe, D. V. Chem. Rev. 1970, 70, 295-322.
7. (g) Olah, G. A.; Dunne, K.; Kelly, D. P.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 7438-7447.
8. (h) Bunton, C. A.; Rubin, R. J. J. Am. Chem. Soc. 1976, 98, 4236-4246.
9. (a) Rhee, E. S.; Shine, H. J. J. Am. Chem. Soc. 1986, 108, 1000-1006.
10. (b) Shine, H. J. In Isotopes in Organic Chemistry; Buncel, E., Saunders, W. H., Jr., Eds.; Elsevier: Amsterdam, 1992; Vol. 8, Chapter 1.
11. -1.
12. -1.
13. 0 = 0.01 M. See the following references for the titration method using Bindschedler's Green. (a) Dewar, M. J. S. J. Chem. Soc. 1946, 777-780. (b) Croce, L. J.; Gettler, J. D. J. Am. Chem. Soc. 1953, 75, 874-879. (c) Cohen, M. D.; Hammond, G. S. J. Am. Chem. Soc. 1953, 75, 880-883. (d) Shine, H. J.; Trisler, J. C. J. Am. Chem. Soc. 1960, 82, 4054-4058. (e) Clovis, J. S.; Hammond, G. S. J. Org. Chem. 1963, 28, 3290-3297.
14. 0 = 0.01 M. See the following references for the titration method using Bindschedler's Green. (a) Dewar, M. J. S. J. Chem. Soc. 1946, 777-780. (b) Croce, L. J.; Gettler, J. D. J. Am. Chem. Soc. 1953, 75, 874-879. (c) Cohen, M. D.; Hammond, G. S. J. Am. Chem. Soc. 1953, 75, 880-883. (d) Shine, H. J.; Trisler, J. C. J. Am. Chem. Soc. 1960, 82, 4054-4058. (e) Clovis, J. S.; Hammond, G. S. J. Org. Chem. 1963, 28, 3290-3297.
15. 0 = 0.01 M. See the following references for the titration method using Bindschedler's Green. (a) Dewar, M. J. S. J. Chem. Soc. 1946, 777-780. (b) Croce, L. J.; Gettler, J. D. J. Am. Chem. Soc. 1953, 75, 874-879. (c) Cohen, M. D.; Hammond, G. S. J. Am. Chem. Soc. 1953, 75, 880-883. (d) Shine, H. J.; Trisler, J. C. J. Am. Chem. Soc. 1960, 82, 4054-4058. (e) Clovis, J. S.; Hammond, G. S. J. Org. Chem. 1963, 28, 3290-3297.
16. 0 = 0.01 M. See the following references for the titration method using Bindschedler's Green. (a) Dewar, M. J. S. J. Chem. Soc. 1946, 777-780. (b) Croce, L. J.; Gettler, J. D. J. Am. Chem. Soc. 1953, 75, 874-879. (c) Cohen, M. D.; Hammond, G. S. J. Am. Chem. Soc. 1953, 75, 880-883. (d) Shine, H. J.; Trisler, J. C. J. Am. Chem. Soc. 1960, 82, 4054-4058. (e) Clovis, J. S.; Hammond, G. S. J. Org. Chem. 1963, 28, 3290-3297.
17. 0 = 0.01 M. See the following references for the titration method using Bindschedler's Green. (a) Dewar, M. J. S. J. Chem. Soc. 1946, 777-780. (b) Croce, L. J.; Gettler, J. D. J. Am. Chem. Soc. 1953, 75, 874-879. (c) Cohen, M. D.; Hammond, G. S. J. Am. Chem. Soc. 1953, 75, 880-883. (d) Shine, H. J.; Trisler, J. C. J. Am. Chem. Soc. 1960, 82, 4054-4058. (e) Clovis, J. S.; Hammond, G. S. J. Org. Chem. 1963, 28, 3290-3297.
18. Shine, H. J.; Chamness, J. T. J. Org. Chem. 1963, 28, 1232-1236.
19. Shine, H. J.; Henderson, G. N.; Cu, A.; Schmid, P. J. Am. Chem. Soc. 1977, 99, 3719-3723.
20. Shine, H. J.; Stanley, J. P. J. Org. Chem. 1967, 32, 905-910.
21. In earlier reports, the ratio 70:30 for 9:10 was quoted; see any reference in ref 1. Recently remeasured ratio of 9 to 10 in 75% aqueous ethanol is 85:15; see ref 10.
22. Subotkowski, W.; Kupczyk-Subotkowska, L.; Shine, H. J. J. Am. Chem. Soc. 1993, 115, 5073-5076.
23. Wiley, R. H.; Smith, N. R. J. Am. Chem. Soc. 1948, 70, 2295-2296.
24. Each rearrangement of 16 and 17 gave p-benzidine-type compound in 21% and 17% isolated yield, respectively, in addition to disproportionation products such as corresponding diazene and fission amine.