Thermochemical Stability of α-Amino-α-carbonylmethyl Radicals and Their Resonance As Measured by ESR

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 552-558

  Welle, Frank M ^a   Beckhaus, Hans Dieter ^a   Rüchardt, Christoph ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000023210     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961703v     Document Type: Article

References (61)

1. Previous communication Welle, F. M.; Verevkin, S. P.; Beckhaus, H.-D.; Rüchardt, C. Liebigs Ann. 1997, 155-163.
2. Rüchardt, C.; Beckhaus, H.-D. Top. Curr. Chem. 1985, 130, 1-22.
3. RSE has to be distinguished from the difference in bond energy ΔBDE between substituted C-C bonds and the corresponding C-C bonds in hydrocarbons because the RSEs have been corrected for substituent interactions in the radical precursor but not the ΔBDEs. For a discussion see: (a) Rüchardt, C. Angew. Chem. 1970, 82, 845-888; Angew. Chem., Int. Ed. Engl. 1970, 9, 830. (b) Nicholas, A. M. de P.; Arnold, D. R. Can. J. Chem. 1984, 62, 1850-1859. (c) Clark, K. B.; Wayner, D. D. M. J. Am. Chem. Soc. 1991, 113, 9363-9365. (d) Clark, K. B.; Wayner, D. D. M.; Demirdij, S. H.; Koch, T. H. J. Am. Chem. Soc. 1993, 115, 2447-2453. (e) Jackson, R. A. Tetrahedron, 1991, 47, 6777-6786.
4. RSE has to be distinguished from the difference in bond energy ΔBDE between substituted C-C bonds and the corresponding C-C bonds in hydrocarbons because the RSEs have been corrected for substituent interactions in the radical precursor but not the ΔBDEs. For a discussion see: (a) Rüchardt, C. Angew. Chem. 1970, 82, 845-888; Angew. Chem., Int. Ed. Engl. 1970, 9, 830. (b) Nicholas, A. M. de P.; Arnold, D. R. Can. J. Chem. 1984, 62, 1850-1859. (c) Clark, K. B.; Wayner, D. D. M. J. Am. Chem. Soc. 1991, 113, 9363-9365. (d) Clark, K. B.; Wayner, D. D. M.; Demirdij, S. H.; Koch, T. H. J. Am. Chem. Soc. 1993, 115, 2447-2453. (e) Jackson, R. A. Tetrahedron, 1991, 47, 6777-6786.
5. RSE has to be distinguished from the difference in bond energy ΔBDE between substituted C-C bonds and the corresponding C-C bonds in hydrocarbons because the RSEs have been corrected for substituent interactions in the radical precursor but not the ΔBDEs. For a discussion see: (a) Rüchardt, C. Angew. Chem. 1970, 82, 845-888; Angew. Chem., Int. Ed. Engl. 1970, 9, 830. (b) Nicholas, A. M. de P.; Arnold, D. R. Can. J. Chem. 1984, 62, 1850-1859. (c) Clark, K. B.; Wayner, D. D. M. J. Am. Chem. Soc. 1991, 113, 9363-9365. (d) Clark, K. B.; Wayner, D. D. M.; Demirdij, S. H.; Koch, T. H. J. Am. Chem. Soc. 1993, 115, 2447-2453. (e) Jackson, R. A. Tetrahedron, 1991, 47, 6777-6786.
6. RSE has to be distinguished from the difference in bond energy ΔBDE between substituted C-C bonds and the corresponding C-C bonds in hydrocarbons because the RSEs have been corrected for substituent interactions in the radical precursor but not the ΔBDEs. For a discussion see: (a) Rüchardt, C. Angew. Chem. 1970, 82, 845-888; Angew. Chem., Int. Ed. Engl. 1970, 9, 830. (b) Nicholas, A. M. de P.; Arnold, D. R. Can. J. Chem. 1984, 62, 1850-1859. (c) Clark, K. B.; Wayner, D. D. M. J. Am. Chem. Soc. 1991, 113, 9363-9365. (d) Clark, K. B.; Wayner, D. D. M.; Demirdij, S. H.; Koch, T. H. J. Am. Chem. Soc. 1993, 115, 2447-2453. (e) Jackson, R. A. Tetrahedron, 1991, 47, 6777-6786.
7. RSE has to be distinguished from the difference in bond energy ΔBDE between substituted C-C bonds and the corresponding C-C bonds in hydrocarbons because the RSEs have been corrected for substituent interactions in the radical precursor but not the ΔBDEs. For a discussion see: (a) Rüchardt, C. Angew. Chem. 1970, 82, 845-888; Angew. Chem., Int. Ed. Engl. 1970, 9, 830. (b) Nicholas, A. M. de P.; Arnold, D. R. Can. J. Chem. 1984, 62, 1850-1859. (c) Clark, K. B.; Wayner, D. D. M. J. Am. Chem. Soc. 1991, 113, 9363-9365. (d) Clark, K. B.; Wayner, D. D. M.; Demirdij, S. H.; Koch, T. H. J. Am. Chem. Soc. 1993, 115, 2447-2453. (e) Jackson, R. A. Tetrahedron, 1991, 47, 6777-6786.
8. RSE has to be distinguished from the difference in bond energy ΔBDE between substituted C-C bonds and the corresponding C-C bonds in hydrocarbons because the RSEs have been corrected for substituent interactions in the radical precursor but not the ΔBDEs. For a discussion see: (a) Rüchardt, C. Angew. Chem. 1970, 82, 845-888; Angew. Chem., Int. Ed. Engl. 1970, 9, 830. (b) Nicholas, A. M. de P.; Arnold, D. R. Can. J. Chem. 1984, 62, 1850-1859. (c) Clark, K. B.; Wayner, D. D. M. J. Am. Chem. Soc. 1991, 113, 9363-9365. (d) Clark, K. B.; Wayner, D. D. M.; Demirdij, S. H.; Koch, T. H. J. Am. Chem. Soc. 1993, 115, 2447-2453. (e) Jackson, R. A. Tetrahedron, 1991, 47, 6777-6786.
9. (a) Fischer, H. Z. Naturforsch. 1964,19a, 866-887.
10. (b) Fischer, H. Z. Naturforsch. 1965, 20a, 428-432.
11. Suryan, M. M.; Stein, S. E. J. Phys. Chem. 1989, 93, 7362-7365.
12. α; r = 0.997.
13. Welle, F.; Verevkin, S. P.; Keller, M.; Deckhaus, H.-D.; Rüchardt, C. Chem. Ber. 1994, 127, 697-710.
14. (a) Schulze, R.; Beckhaus, H.-D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031-1038.
15. (b) Schulze, R.; Beckhaus, H.-D.; Rüchardt, C. J. Prakt. Chem. 1990, 332, 325-330.
16. For a discussion of the captodative effect see: Sustmann, R.; Korth, H.-G. Adv. Phys. Org. Chem. 1990, 26, 131-178.
17. -1.
18. (b) For a collection of data see: Welle, F. M. Dissertation, University of Freiburg, Germany, 1996.
19. Hellmann, G.; Hellmann, S.; Beckhaus, H.-D.; Rüchardt, C. Chem. Ber. 1982, 115, 3364-3383.
20. Rakus, K.; Verevkin, S. P.; Peng, W.-H.; Beckhaus, H.-D.; Rüchardt, C. Liebigs Ann. 1995, 2059-2067.
21. Korth, H.-G.; Sustmann, R.; Merenyi, R.; Viehe, H. G. J. Chem. Soc. Perkin Trans. 2 1983, 67-74.
22. Birkhofer, H.; Beckhaus, H.-D.; Rüchardt, C. In Substituent effects in Radical Chemistry; Viehe, H. G.; Janousek, Z.; Merenyi, R., Eds.; NATO ASI Series C 189; Reidel Publishing Company: Dordecht, 1986, p 199.
23. Leroy, G.; Sana, M.; Wilante, C. J. Mot. Struct. 1991, 234, 303-328.
24. Pasto, D. J. J. Am. Chem. Soc. 1988, 110, 8164-8175.
25. (a) Bordwell, F. G.; Lynch, T.-Y. J. Am. Chem. Soc. 1989, 111, 7558-7562.
26. (b) Alnajjar, A.; Gleicher, G.; Franz, J.; Truksa, S.; Zhang, X.-M.; Bordwell, F. Prep. Pap. Am. Chem. Soc. Div. Fuel. Chem. 1994, 39, 635-637.
27. Korth, H.-G.; Trill, H.; Sustmann, R. J. Am. Chem. Soc. 1981, 103, 4483-4489.
28. McInnes, I.; Walton, J. C.; Nonhebel, D. C. J. Chem. Soc., Perkin Trans. 2 1987, 1789-1794.
29. Golde, G.; Möbius, K.; Kaminsky, W. Z. Naturforsch. 1969, 24a, 1214-1217.
30. Griller, D.; Nonhebel, D. C.; Walton, J. C. J. Chem. Soc., Chem. Commun. 1982, 059-1060.
31. Griller, D.; Nonhebel, D. C.; Walton, J. C. J. Chem. Soc., Perkin Trans. 2, 1983, 1373-1379.
32. McInnes, I.; Walton, J. C.; Nonhebel, D. C. J. Chem. Soc., Chem. Commun. 1985, 712-713.
33. Nonhebel, D. C.; Walton, J. C. J. Chem. Soc., Chem. Commun. 1984, 731-732.
34. Paul, H.; Fischer, H. Helv. Chim. Acta 1973, 56, 1575-1594.
35. Gleissner, R. Dissertation, University of Freiburg, Germany, 1988.
36. Gilbert, B. C.; Norman, R. O. C.; Placucci, G.; Sealy, R. C. J. Chem. Soc., Perkin Trans. 2 1975, 885-891.
37. Pakusch, J.; Beckhaus, H.-D. Chem. Ber. 1991, 124, 1191-1198.
38. Schüle, U. Dissertation, University of Freiburg, Germany, 1992.
39. Wood, D. E.; Lloyd, R. V. J. Chem. Phys. 1970, 53, 3932-3942.
40. (a) Birkhofer, H.; Beckhaus, H.-D.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 185-188.
41. (b) Birkhofer, H.; Beckhaus, H.-D.; Rüchardt, C. Chem. Ber. 1993, 126, 1023-1030.
42. (c) Birkhofer, H.; Beckhaus, H.-D.; Peters, K.; von Schnering, H.-G.; Rüchardt, C. Chem. Ber. 1993, 126, 1693-1699.
43. Dobbs, A. J.; Gilbert, B. C.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1972, 786-794.
44. Rakus, K; Verevkin, S. P.; Beckhaus, H.-D.; Rüchardt, C. Chem. Ber. 1994, 127, 2225-2234.
45. Kubiak, B.; Lehnig, M.; Neumann, W. P.; Pentling, U.; Zarkadis, A. K. J. Chem. Soc., Perkin Trans. 2 1992, 1443-1447.
46. Korth, H.-G.; Sustmann, R.; Merenyi, R.; Viehe, H. G. J. Chem. Soc., Perkin Trans. 2, 1983, 67-74.
47. Nölke, M.; Beckhaus, H.-D.; Rüchardt, C. Liebigs Ann. 1995, 41-51.
48. Kratt, G.; Beckhaus, H.-D.; Rüchardt, C. Chem. Ber. 1984, 117, 1748-1764.
49. (a) Herberg, C.; Verevkin, S. P.; Nölke, M.; Beckhaus, H.-D.; Rüchardt, C. Liebigs Ann. 1995, 512-522.
50. (b) Herberg, C. Dissertation, University of Freiburg, Germany, 1992.
51. Kochi, J. K.; Krucic, P. J. J. Am. Chem. Soc. 1968, 90, 7157-7159.
52. Rakus, K.; Schätzer, J.; Verevkin, S.; Beckhaus, H.-D.; Rüchardt, C. Chem. Ber. 1994, 127, 1095-1103.
53. Atto, A.; Hudson, A.; Jackson, R. A.; Simmons, N. P. C. Chem. Phys. Lett. 1975, 33, 477-478.
54. Schulze, R. Dissertation, University of Freiburg, Germany, 1992.
55. Herberg, C.; Beckhaus, H.-D.; Rüchardt, C. Chem. Ber. 1994, 127, 2065-2072.
56. Leroy, G.; Peeters, D.; Sana, M.; Wilante, C. Bull. Soc. Chim. Belg. 1988, 97, 1003-1010.
57. Wood, D. E.; Lloyd, R. V. J. Chem. Phys. 1970, 53, 3932-3942.
58. Crowell, T. I.; Helsy, G. C.; Lutz, R. E.; Scott, W. L. J. Am. Chem. Soc. 1963, 85, 443-446.
59. Fitzpatrick, J. E.; Milner, D. J.; White, P. Synth. Commun. 1982, 12, 489-494.
60. Ohmes, E.; Kothe, G.; Naujok, A.; Zimmermann, H. Ber. Bunsenges. 1971, 75, 895-901.
61. Allinger, N. L.; Yuh, Y. H. QCPE 395.