Detection of Aryl Radicals in Hydrodediazoniations

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8304-8308

  Wassmundt, Frederick W ^a   Kiesman, William F ^a,b  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b BIOGEN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000955016     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962128y     Document Type: Article

References (39)

1. (a) Kornblum, N. A.; Cooper, G. D.; Taylor, J. E. J. Am. Chem. Soc. 1950, 72, 3013. Kornblum, N. Org. React. 1944, 2, 262.
2. (a) Kornblum, N. A.; Cooper, G. D.; Taylor, J. E. J. Am. Chem. Soc. 1950, 72, 3013. Kornblum, N. Org. React. 1944, 2, 262.
3. (b) Wulfman, D. S. The Chemistry of Diazonium and Diazo Groups. In The Chemistry of the Functional Groups; Patai, S., Ed.; Wiley: New York, 1978; pp 286-287.
4. (c) Hegarty, A. F., ref 1b, pp 564-565.
5. (d) Saunders, K. H.; Allen, R. L. M. Aromatic Diazo Compounds, 3rd ed.; Edward Arnold: London, 1985; pp 537-548.
6. (e) Zollinger, H. Diazo Chemistry I: Aromatic and Heteroaromatic Compounds; VCH: New York, 1994.
7. Walling, C. Free Radicals in Solution; Wiley: New York, 1957; p 155, 255.
8. Bunnett, J. F.; Wamser, C. C. J. Am. Chem. Soc. 1966, 88, 5534. Brydon, D. L.; Cadogen, J. I. G. J. Chem. Soc. C. 1968, 819. Broxton, T. J.; Bunnett, J. F.; Paik, C. H. J. Org. Chem. 1977, 42, 643.
9. Bunnett, J. F.; Wamser, C. C. J. Am. Chem. Soc. 1966, 88, 5534. Brydon, D. L.; Cadogen, J. I. G. J. Chem. Soc. C. 1968, 819. Broxton, T. J.; Bunnett, J. F.; Paik, C. H. J. Org. Chem. 1977, 42, 643.
10. Bunnett, J. F.; Wamser, C. C. J. Am. Chem. Soc. 1966, 88, 5534. Brydon, D. L.; Cadogen, J. I. G. J. Chem. Soc. C. 1968, 819. Broxton, T. J.; Bunnett, J. F.; Paik, C. H. J. Org. Chem. 1977, 42, 643.
11. Wassmundt, F. W.; Kiesman, W. F. J. Org. Chem. 1995, 60, 1713.
12. (a) Werner, R.; Rüchardt, C. Tetrahedron Lett. 1969, 28, 2407.
13. (b) Rüchardt, C.; Merz, E.; Freudenburg, B.; Opgenorth, H. J.; Tan, C. C.; Werner, R. Free-radical Reactions of Aromatic Diazonium Salts. In Essays on Free-radical Chemistry, Spec. Publ. 24; The Chemical Society: London, 1970; pp 56-66.
14. Besse, J.; Zollinger, H. Helv. Chim. Acta 1981, 64, 532, 537.
15. In unpublished work, phenylacetic acid was isolated from the reaction mixtures of trapping experiments during the examination of Gomberg-Bachmann arylations in benzene. This result traces the fate of the alkyl radical generated in eq 2.
16. Swain, C. G.; Rogers, R. J. J. Am. Chem. Soc. 1975, 97, 799.
17. Beckwith, A. L. J. Aust. J. Chem. 1972, 25, 1887.
18. Levit, A. F.; Kiprianova, L. A.; Gragerov, I. P. Zh. Org. Khim. 1975, 11, 2351; Chem. Abstr. 1975, 84, 42954d.
19. Levit, A. F.; Kiprianova, L. A.; Gragerov, I. P. Zh. Org. Khim. 1975, 11, 2351; Chem. Abstr. 1975, 84, 42954d.
20. Hodgson, H. H.; Kershaw, A. J. Chem. Soc. 1930, 2784.
21. Bunnett, J. F.; Yijima, C. J. Org. Chem. 1977, 42, 639.
22. Andersen, M. L.; Handoo, K. L.; Parker, V. D. Acta Chem. Scand. 1991, 45, 983.
23. Bagotzky, V. S.; Vasilyev, Y. B. Electrochim. Acta 1964, 9, 869.
24. Tröndlin, F.; Rüchardt, C. Chem. Ber. 1977, 110, 2494.
25. Doyle, M. P.; Dellaria, J. F.; Siegfried, B.; Bishop, S. W. J. Org. Chem. 1977, 42, 3494.
26. Pedemonte, R. P. Ph.D. Dissertation, University of Connecticut, 1991. Wassmundt, F. W.; Pedemonte, R. P. J. Org. Chem. 1995, 60, 4991.
27. Pedemonte, R. P. Ph.D. Dissertation, University of Connecticut, 1991. Wassmundt, F. W.; Pedemonte, R. P. J. Org. Chem. 1995, 60, 4991.
28. Wassmundt, F. W.; Kiesman, W. F. J. Org. Chem. 1995, 60, 196.
29. The product-forming and chain-propagating steps of the hydrodediazoniations in THF are best accommodated by the mechanism described in Cadogan, J. I. G.; Molina, G. A. J. Chem. Soc., Perkin Trans. 1 1973, 541.
30. Rutherford, K. G.; Redmond, W. A. J. Org. Chem. 1963, 28, 568.
31. DeTar, D. F.; Kosuge, T. J. Am. Chem. Soc. 1958, 80, 6072.
32. Meerwein, H.; Allendörfer, H.; Beekmann, P; Kunert, F.; Morschel, H.; Pawellek, F.; Wunderlich, K. Angew. Chem. 1958, 70, 211.
33. Threadgill, M. D.; Gledhill, A. P. J. Chem. Soc., Perkin Trans. 1 1986, 873.
34. Hayon, E.; Ibata, T.; Lichtin, N. N.; Simic, M. J. Am. Chem. Soc. 1970, 92, 2, 3898.
35. (a) Kochi, J. K. J. Am. Chem. Soc. 1957, 79, 2942.
36. (b) Dickerman, S. C.; Weiss, K.; Ingberman, A. K. J. Am. Chem. Soc. 1958, 80, 1904.
37. (c) Dickerman, S. C.; DeSouza, D. J.; Jacobson, N. J. Org. Chem. 1969, 34, 710.
38. (d) Galli, C. J. Chem. Soc., Perkin Trans. 2 1981, 1459.
39. (e) Galli, C. J. Chem. Soc., Perkin Trans. 2 1982, 1139.