A Force-Field Model for Intramolecular Radical Additions

Journal of Organic Chemistry

Volumn 52, Issue 6, 1987, Pages 959-974

  Spellmeyer, D C ^a   Houk, K N ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845282341     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00382a001     Document Type: Article

References (33)

1. Allinger, N. L.; Yuh, Y. QCPE 1980,12, 395. Burkert, U.; Allinger, N. L. Molecular Mechanics; American Chemical Society: Washington, DC, 1982.
2. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron Lett. 1985, 26, 373; Tetrahedron 1985, 41, 3925.
3. Hart, D. J. Science (Washington, D. C.) 1984, 223, 883. Stork, G. In Current Trends in Organic Synthesis; Nozaki, H., Ed.; Pergamon: New York. 1983; Pp359ff and references therein.
4. Curran, D.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448; Tetrahedron 1985. 41, 3943.
5. Wilcox, C. S.; Thomasco, L. M. J. Org. Chem. 1985, 50, 546 and references therein.
6. For recent reviews, see: (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; pp 162–283. (b) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073 and references therein, (c) Surzur, J. M. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum: New York, 1981; Vol. 2, Chapter 3. (d) Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317.
7. Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482. Beckwith, A. L. J.; Lawrence, T.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 484.
8. Houk, K. N.; Rondan, N. G.; Wu, Y. D. ; Metz, J. T.; Paddon-Row, M. N. Tetrahedron 1984, 40, 2257. (b) Houk, K. N.; Moses, S. R.; Wu, Y. D. ; Rondan, N. G.; Jager, V.; Schohe, R.; Fronczek, F. R. J. Am. Chem. Soc. 1984,106, 3380. (c) Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y. D. ; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Lon-charich, R. J. Science (Washington, D. C.) 1986, 231, 1108 and references therein, (d) Brown, F. K.; Houk, K. N. Tetrahedron Lett. 1985, 26, 2297. (e) Brown, F. K.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 1971.
9. Houk, K. N.; Paddon-Row, M. N.; Spellmeyer, D. C.; Rondan, N. G.; Nagase, S. J. Org. Chem. 1986, 51, 2874.
10. Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162.
11. Imam, M. R.; Allinger, N. L. J. Mol. Struct. 1985, 126, 345.
12. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939.
13. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10. 1.
14. Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753. Giese, B. Angew. Chem., Int. Ed. Engl. 1985, 24, 553.
15. Poblet, J. M.; Canadell, E. Can. J. Chem. 1983, 61, 2068. See also, Delbecq, F.; Ilavsky, D.; Anh, N. T.; Lefour, J. M. J. Am. Chem. Soc. 1985, 107, 1623.
16. Bischof, P. Helv. Chim. Acta 1980, 63, 1434.
17. Julia, M.; Descoins, C.; Baillarge, M.; Jacquet, B.; Uguen, D.; Groeger, F. A. Tetrahedron 1975, 31, 1737. LeBel had suggested this hypothesis in a discussion with Julia, as mentioned in this paper.
18. Capon, B.;Rees, C. W. Ann. Rep. Chem. Soc. 1964, 61, 221.
19. Canadell E.; Igual, J. J. Chem. Soc., Perkin Trans. 2 1985, 1331.
20. Hart, D. J.: Tsai. Y. M. J. Am. Chem. Soc. 1984. 106, 8209.
21. Surzur, J. M.; Bertrand, M. P.; Nauguier, R. Tetrahedron Lett. 1969, 4197.
22. Smith, T. W.; Butler, G. B. J. Org. Chem. 1978, 43, 6.
23. Padwa, A.; Nimmesgern, H.; Wong, G. S. K. Tetrahedron Lett. 1985, 26, 957.
24. Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Chem. Commun. 1974, 472.
25. Struble, D. L.; Beckwith, A. L. J.; Gream, G. E. Tetrahedron Lett. 1968, 34, 3701. Beckwith, A. L. J.; Gream, G. E.; Struble, D. L. Aust. J. Chem. 1972, 25, 1081.
26. Beckwith, A. L. J.; Blair, I. A.; Phillipou, G. Tetrahedron Lett. 1974, 26, 2251; J. Am. Chem. Soc. 1974, 96, 1613.
27. Wolff, S.; Agosta, W. C. J. Chem. Res. Synop. 1981, 78.
28. Corey, E. J.; Shimoji, K.; Shih, C. J. Am. Chem. Soc. 1984,106, 6425.
29. Clive, D. L. J.; Beaulieu, P. L. J. Chem. Soc., Chem. Commun. 1983, 307.
30. Binkley, J. S.; Frisch, M.; Krishnan, R.; DeFrees, D.; Schlegel, H. B.; Whiteside, R. A.; Fluder, E.; Seeger, R.; Pople, J. A. “GAUSSIAN 82 Releases E and H” Carnegie-Mellon University: Pittsburgh, PA, 1982. (b) Binkley, J. S.; Whiteside, R. A.; Krishnan, R.; Seeger, R.; DeFrees, D.; Schlegel, H. B.; Topiol, S.; Kahn, L. R.; Pople, J. A. “GAUSSIAN 80”, CarneeieMellon University: Pittsburgh, PA.
31. Beckwith, A. L. J.; Lawrence, T. J. Am. Chem. Soc., Perkin Trans. 2 1979. 1535.
32. Walling, C.; Cioffari, A. J. Am. Chem. Soc. 1972, 94, 6064.
33. Beckwith, A. L. J.; Phillipou, G.; Serelis, A. K. Tetrahedron Lett. 1981, 22, 2811.