Effect of Substituants on the Structure of the Vinyl Radical: Calculations and Experiments

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 4072-4077

  Galli, Carlo ^a   Guarnieri, Alessandra ^a   Koch, Heinz ^b   Mencarelli, Paolo ^a   Rappoport, Zvi ^c  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b ITHACA COLLEGE   (United States)

^c HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001304578     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962373h     Document Type: Article

References (67)

1. Galli, C.; Gentili, P.; Guarnieri, A.; Rappoport, Z. J, Org. Chem. 1996, 61, 8878.
2. (a) Bunnett, J. F. Acc. Chem. Res. 1978, 11, 413.
3. RN1 Mechanism; ACS Monograph 178; American Chemical Society: Washington, DC, 1983.
4. (c) Rossi, R. A.; Pierini, A. B.; Peñéñory, A. B. In The Chemistry of Functional Groups. Supplement D2: The Chemistry of Halides, Pseudohalides and Azides; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1995; Chapter 24.
5. (a) Miller, S. I.; Lee, W. G. J. Am. Chem. Soc. 1959, 81, 6313.
6. (b) Walborsky, H. M.; Turner, L. M. Ibid. 1972, 94, 2273.
7. (c) Corey, E. J.; Ulrich, P.; Fitzpatrick, J. M. Ibid. 1976, 98, 222.
8. (d) Froelicher, S. W.; Freiser, B. S.; Squires, R. R. Ibid. 1986, 108, 2853. Here, an E - Z isomerization barrier of 26.6 kcal/mol for 1-propenyl ions is calculated.
9. (e) Chou, P. K.; Kass, S. R. Ibid. 1991, 113, 4357.
10. (a) Mayr, H.; Schneider, R.; Wilhelm, D.; Schleyer, P. v. R. J. Org. Chem. 1981,46, 5336,
11. (b) Rappoport, Z. In Reactive Intermediates; Abramovitch R. A., Ed.; Plenum Press: New York, 1983; Vol. 3, pp 427-615.
12. (c) Berkowitz, J.; Mayhew, C. A.; Ruscic, B. J. Chem, Phys. 1988, 88, 7397.
13. fd) Lindh, R.; Rice, J. E.; Lee, T. J, Ibid. 1991, 94, 8008.
14. Jenkins, P. R.; Symons, M. C. R.; Booth, S. E.; Swain, C. J. Tetrahedron Lett. 1992, 33, 3543.
15. Gillespie, R. J. Chem. Soc. Rev. 1992, 21, 59.
16. (a) Fessenden, R. W,; Schuler, R. H. J. Chem. Phys. 1963, 39, 2147.
17. (b) Cochran, E. L.; Adrian, F. J.; Bowers, V. A. Ibid. 1964, 40, 213.
18. (c) Fessenden, R. W. Ibid. 1967, 71, 74.
19. (a) Bonazzola, L.; Feinstein, S.; Marx, R. Mol. Phys. 1971, 22, 689.
20. (b) Neilson, G. W.; Symons, M. C. R. J. Chem. Soc., Perkin Trans. 2 1973, 1405.
21. (c) Kasai, P. H.; Whipple, E. B. J. Am. Chem. Soc. 1967, 89, 1033.
22. (d) Bennett, J. E.; Howard, J. A. Chem. Phys. Lett. 1971, 9, 460.
23. (e) Panek, E. J.; Kaiser, L. R.; Whiteside, G. M. J. Am. Chem. Soc. 1977, 99, 3708.
24. (f) Rubin, H.; Fischer, H. Helv. Chim. Acta 1996, 79, 1670.
25. Rhodes, C. J.; Roduner, E. J. Chem. Soc., Perkin Trans. 2 1990, 1729.
26. (a) Liu, M. S.; Soloway, S.; Wedegaertner, D. K.; Kampmeier, J. A. J. Am. Chem. Soc. 1971, 93, 3809.
27. (b) Singer, L. A.; Kong, N. P. Tetrahedron Lett. 1967, 643.
28. Metzger, J. O.; Blumenstein, M. Chem. Ber. 1993, 126, 2493.
29. Korth, H.-G.; Lusztyk, J.; Ingold, K. U. J. Chem. Soc., Perkin Trans. 2 1990, 1997.
30. Paddon-Row, M. N.; Pople, J. A. J. Phys. Chem. 1985, 89, 2768.
31. (a) Galli, C.; Gentili, P.; Rappoport, Z. J. Org. Chem. 1994, 59, 6786.
32. (b) Amatore, C.; Galli, C.; Gentili, P.; Guamieri, A.; Schottland, E.; Rappoport, Z. J. Chem. Soc., Perkin Trans. 2 1995, 2341.
33. Simamura, O. Top, Stereochem. 1969, 4, 1.
34. Bartolotti, L. J.; Flurchick, K. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH Publishers: New York, 1996; Vol 7, Chapter 4.
35. (a) Barone, V.; Adamo, C.; Russo, N. Chem. Phys. Lett. 1993, 212, 5.
36. (b) Barone, V.; Adamo, C.; Russo, N. Int. J. Quantum Chem. 1994, 52, 963.
37. Guerra, M. Res. Chem. Intermed. 1996, 22, 369.
38. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gordon, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92/DFT, Revision F.2; Gaussian, Inc.: Pittsburgh, PA, 1993.
39. Frisch, M. J.; Trucks, G. W.; Schlegel H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision C.2; Gaussian, Inc.: Pittsburgh PA, 1995.
40. Becke, A. D. Phys. Rev. A 1988, 38, 3098,
41. Lee, C.; Yang, W.; Parr, G. Phys. Rev. B 1988, 37, 785.
42. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem,. Phys. Lett. 1989, 157, 200.
43. Copyright 1993-1994 Pavel V. Ganelin. All rights reserved,
44. Bergman, D.; Hinze, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 150.
45. Curran, D. P. Synthesis 1988, 417.
46. Haar, V. R., Jr. Thesis, University of Iowa (1973); University Microfilms 74-16, 693.
47. (a) Becker, E. D. In High Resolution NMR: Academic Press: New York, 1980; 2nd Ed.; Chapter 5.
48. (b) Masure, D.; Sauvetre, R.; Normant, J. F.; Villieras, J. Synthesis 1976, 761.
49. Ogawa, A.; Yokoyama, K.; Yokoyama, H.; Obayashi, R.; Karabe, N.; Sonoda, N. J. Chem. Soc., Chem. Commun. 1991, 1748.
50. Curran, D. P.; Jasperse, C. P.; Totleben, M. J. J. Org. Chem. 1991, 56, 7169.
51. Yamataka, H.; Rappoport, Z. Work in progress.
52. (a) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 18, 809.
53. (b) Wiberg, K. B. Acc. Chem. Res. 1996, 29, 229.
54. Boche, G.; Walborsky, H. M. In Cyclopropane derived radical intermediates; updates from The Chemistry of Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1990; Chapters 1 and 3.
55. Fessenden, R. W.; Schuler, R. H. J, Chem. Phys. 1965, 43, 2704.
56. Johnston, L. J.; Lusztyk, J.; Wayner, P. P. M.; Abeywickrema, A. N.; Beckwith, A. L. J.; Scaiano, J. C.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 4594.
57. Apeloig, Y.; Nakash, M. J. Am. Chem. Soc. 1994, 116, 10781.
58. Hart, H.; Martin, R. A. J. Am. Chem. Soc. 1960, 82, 6362.
59. Altman, L. J.; Baldwin, R. C. Tetrahedron Lett. 1971, 2531.
60. Guerra, M. J. Phys. Chem. 1995, 99, 81.
61. Guerra, M. J. Am. Chem. Soc. 1993, 115, 11926.
62. (a) Hoffmann, R.; Lipscomb, W. N. J. Chem. Phys. 1962, 36, 2179, 3498.
63. (b) Pauling, L. Ibid. 1969, 57, 2767.
64. (c) Wells, P. R. Prog. Phys. Org. Chem. 1968, 6, 111.
65. (d) Bingham, R. C.; Dewar, M. J. S. J. Am. Chem. Soc. 1973, 95, 7180.
66. Guerra, M. J. Chem. Soc., Perkin Trans. 2 1996, 779.
67. Guerra, M. Chem. Phys. Lett. 1995, 237, 61.