Structural Distortions of Cyclic Phosphoranes and the Berry Exchange Coordinate. A Quantitative Description1

Journal of the American Chemical Society

Volumn 99, Issue 10, 1977, Pages 3318-3326

  Holmes, Robert R ^a   Deiters, Joan A ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847088523     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00452a021     Document Type: Article

References (54)

1. Pentacoordinated Molecules. 21. Previous paper in this series: R. R. Holmes, J. Am. Chem. Soc., 97, 5379 (1975).
2. D. Hellwinkel, “Organo Phosphorus Compounds”, Vol. 3, G. M. Kosolapoff and L. Maier, Ed., Wiley-lnterscience, New York, N.Y., 1972, p 185.
3. R. S. Berry, J. Chem. Phys., 32, 933 (1960).
4. D. Z. Denney, D. W. White, and D. B. Denney, J. Am. Chem. Soc., 93, 2066 (1971).
5. a) P. Gillespie, P. Hoffmann, H. Klusacek, D. Marquarding, S. Pfohl, F. Ramirez, E. A. Tsolis, and I. Ugi, Angew. Chem., Int. Ed. Engl., 10, 687 (1971);
6. F. Ramirez and I. Ugi, Adv. Phys. Org. Chem., 9, 256 (1971);
7. I. Ugi, F. Ramirez, D. Marquarding, H. Klusacek, and P. Gillespie, Acc. Chem. Res., 4, 288 (1971);
8. F. Ramirez and I. Ugi, Bull. Soc. Chlm. Fr., 453 (1974).
9. a) H. Wunderlich, D. Mootz, R. Schmutzler, and M. Wieber, Z. Naturforsch. B, 29, 32 (1974);
10. H. Wunderlich, Acta Crystallogr., Sect. B, 30, 939 (1974);
11. H. Wunderlich and D. Mootz, J. Am. Chem. Soc., 30, 935 (1974).
12. R. R. Holmes, J. Am. Chem. Soc., 96, 4143 (1974).
13. E. L. Muetterties and L. J. Guggenberger, J. Am. Chem. Soc., 96, 1748 (1974).
14. a) R. K. Brown and R. R. Holmes, J. Am. Chem. Soc., 99, 3326 (1977);
15. P. F. Meunier, J. A. Deiters, and R. R. Holmes, Inorg. Chem., 15, 2572 (1976);
16. P. F. Meunier, J. R. Devillers, and R. R. Holmes, work submitted for publication.
17. J. R. Devillers and R. R. Holmes, J. Am. Chem. Soc., 99, 3332 (1977).
18. J. A. Deiters, J. C. Gallucci, T. E. Clark, and R. R. Holmes, work submitted for publication.
19. R. Sarma, F. Ramirez, and J. F. Maracek, J. Org. Chem., 41, 473 (1976).
20. D. D. Swank, C. N. Caughlan, F. Ramirez, and J. F. Pilot, J. Am. Chem. Soc., 93, 5236 (1971).
21. R. Sarma, F. Ramirez, B. McKeever, J. F. Maracek, and S. Lee, J. Am. Chem. Soc., 98, 581 (1976).
22. a) W. C. Hamilton, S. J. LaPlaca, and F. Ramirez, J. Am. Chem. Soc., 87, 127 (1965);
23. R. D. Spratley, W. C. Hamilton, and J. Ladell, J. Am. Chem. Soc., 89, 2272 (1967).
24. a) W. C. Hamilton, J. S. Ricci, Jr., F. Ramirez, L. Kramer, and P. Stern, J. Am. Chem. Soc., 95, 6335 (1973);
25. H. L. Carrell, H. M. Berman, J. S. Ricci, Jr., W. C. Hamilton, F. Ramirez, J. F. Marecek, L. Kramer, and I. Ugi, J. Am. Chem. Soc., 97, 38 (1975).
26. D. Hellwinkel, W. Krapp, D. Schomburg, and W. S. Sheldrick Z. Naturforsch. B, 31, 948 (1976).
27. a) W. S. Sheldrick, A. Schmidpeter, and J. H. Weinmaier, Angew, Chem., 87, 519 (1975);
28. W. S. Sheldrick, Acta Crystallogr., Sect. B, 32, 925 (1976).
29. W. S. Sheldrick, personal communication; A. Schmidpeter, D. Schomburg, W. S. Sheldrick, and J. H. Weinmaier, Angew. Chem., 88, 851 (1976).
30. a) A. Rauk, L. C. Allen, and K. Mislow, J. Am. Chem. Soc., 94, 3035 (1972); (b) R. Hoffmann, J. M. Howell, and E. L. Muetterties, J. Am. Chem. Soc., 94, 3047 (1972); (c) L. S. Bartell and V. Plato, J. Am. Chem. Soc., 95, 3097 (1973);
31. A. Strich and A. Veillard, J. Am. Chem. Soc., 95, 5574(1973).
32. a) R. R. Holmes, Acc. Chem. Res., 5, 296 (1972);
33. R. R. Holmes, L. S. Couch, and C. J. Hora, Jr., J. Chem. Soc., Chem. Commun., 197 (1974).
34. L. S. Bernstein, J. J. Kim, K. S. Pitzer, S. Abramowitz, and I. Levin, 30th Symposium on Molecular Structure and Spectroscopy. The Ohio State University, Columbus, Ohio, June 1975, Abstract No. TA6; L, S. Bernstein, S. Abramowitz, and I. W. Levin, J. Chem. Phys., 64, 3228 (1976);
35. L. S. Bernstein, J. J. Kim, K. S. Pitzer, S. Abramowitz, and I. W. Levin, J. Am. Chem. Soc., 62, 3671 (1975).
36. a) L. S. Bartell, inorg. Chem., 9, 1594 (1970); (b)K. W. Hansen and L. S. Bartell, J. Am. Chem. Soc., 4, 1775 (1965);
37. L. S. Bartell and K. W. Hansen, J. Am. Chem. Soc., 4, 1777 (1965);
38. F. B. Clippard, Jr., and L. S. Bartell, L. S. Bartell, 9, 805 (1970);
39. W. J. Adams and L. S. Bartell, J. Mot. Struct., 8, 23 (1971);
40. H. Yow and L. S. Bartell, J. Am. Chem. Soc., 15, 209 (1973).
41. a) J. E. Griffiths, R. P. Carter, Jr., and R. R. Holmes, J. Chem. Phys., 41, 863(1964);
42. I. W. Levin, J. Am. Chem. Soc., 50, 1031 (1969);
43. F. A. Miller and R. J. Capwell, Spectrochim. Acta, Part A, 27, 125 (1971);
44. I. W. Levin, J. Mot. Spectrosc., 33, 61 (1970).
45. a) F. H. Westheimer, Acc. Chem. Res., 1, 70 (1968);
46. E. L. Muetterties, W. Mahler, and R. Schmutzler, inorg. Chem., 2, 613 (1963);
47. E. L. Muetterties, W. Mahler, K. J. Packer, and R. Schmutzler, J. Am. Chem. Soc., 3, 1298 (1964).
48. J. A. Howard, D. R. Russell, and S. Trippett, J. Chem. Soc., Chem. Commun., 856 (1973).
49. A. Schmidpeter, J. Luber, D. Schomburg, and W. S. Sheldrick, Chem. Ber., in press.
50. M.-UI-Haque, C. N. Caughlan, F. Ramirez, J. F. Pilot, and C. P. Smith, J. Am. Chem. Soc., 93, 5229 (1971).
51. K. Mislow, Acc. Chem. Res., 3, 321 (1970).
52. a) D. Gorenstein and F. H. Westheimer, J. Am. Chem. Soc., 92, 634 (1970);
53. D. Gorenstein, J. Am. Chem. Soc., 92, 644 (1970).
54. F. Ramirez, Acc. Chem. Res., 1, 168 (1968).