Cyclic Aminophosphites and -phosphoranes Possessing Six- and Higher-Membered Rings: A Comparative Study of Structure and Reactivity

Inorganic Chemistry

Volumn 36, Issue 10, 1997, Pages 2044-2051

  Said, Musa A ^a   Pülm, Melanie ^b   Herbst Irmer, R ^b   Kumara Swamy, K C ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001022907     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9611958     Document Type: Article

References (51)

1. (a) Bentrude, W. G. In Phosphorus-31 NMR-Spectral Properties in Compound Characterization and Structural Analysis, Quin, L. D., Verkade, J. G., Eds.; VCH: New York, 1994; Chapter 4.
2. (b) Yu, J. H.; Arif, A. M.; Bentrude, W. G. J. Am. Chem. Soc. 1990, 112, 7451.
3. Yu, J. H.; Sopchik, A. E.; Arif, A. M.; Bentrude, W. G. J. Org. Chem. 1990, 55, 3444.
4. Breeders, N. L. H. L.; Koole, L. H.; Buck, H. M. J. Am. Chem. Soc. 1990, 112, 7475.
5. (a) Holmes, R. R.; Kumara Swamy, K. C.; Holmes, J. M.; Day, R. O. Inorg. Chem, 1991, 30, 1052.
6. (b) Prakasha, T. K.; Day, R. O.; Holmes, R. R. J. Am, Chem. Soc. 1994, 116, 8095.
7. (a) Burton, S. D.; Kumara Swamy, K. C.; Holmes, J. M.; Day, R. O.; Holmes, R. R. J. Am. Chem. Soc. 1990, 112, 6104.
8. (b) Kumara Swamy, K. C.; Day, R. O.; Holmes, J. M.; Holmes, R. R. J. Am. Chem. Soc. 1990, 112, 6095.
9. Prakasha, T. K.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1992, 31, 725.
10. Prakasha, T. K.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1992, 31, 1913.
11. (e) Prakasha, T. K.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1992, 31, 3391.
12. (f) Prakasha, T. K.; Burton, S. D.; Day, R. O.; Holmes, J. M.; Holmes, R. R. Inorg. Chem. 1992, 31, 5494.
13. (g) Prakasha, T. K.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1995, 34, 1243.
14. Hans, J.; Day, R. O.; Howe, L.; Holmes, R. R. Inorg. Chem. 1992, 31, 1279.
15. (a) Day, R. O.; Kumara Swamy, K. C.; Fairchild, L.; Holmes, J. M.; Holmes, R. R. J. Am. Chem. Soc. 1991, 113, 1627.
16. (b) Hans, J.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1991, 30, 3928.
17. (a) Maryanoff, B. E.; Huchins, R. O.; Maryanoff, C. A. Top. Stereochem. 1979, 11, 187.
18. (b) Gallagher, M. J. In Phosphorus-31 NMR Spectroscope in Stereochemical Analysis; Verkade, J. G., Quin, L. D., Eds.; VCH: Deerfield Beach, FL, 1987; Chapter 9.
19. Bentrude, W. G.; Setzer, W. N. In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis; Verkade, J. G., Quin, L. D., Eds.; VCH: Deerfield Beach, 1987; Chapter 11 and references cited therein.
20. Schiff, D. E.; Richardson, J. W., Jr.; Jacobson, R. A.; Cowley, A. H.; Lasch, J.; Verkade, J. G. Inorg. Chem. 1984, 23, 3373.
21. 2O). Such an observation has been ascribed to a combination of an electronegativity effect and a steric effect: Hans, J.; Day, R. O.; Howe, L.; Holmes, R. R. Inorg. Chem. 1991, 30, 3132.
22. Holmes, R. R.; Deiters, J. A. Inorg. Chem. 1994, 53, 3235 and references cited therein.
23. (a) Nifant'ev, E. E.; Koroteev, M. P.; Pugashova, N. M.; Kukhareva, T. S.; Borisenko, A. A. Th. Obshch. Khim. 1981, 51, 1900 [Engl. ed. p 1632 (1982)].
24. (b) Nelson, K. A.; Bentrude, W. G.; Setzer, W. N.; Hutchinson, J. P. J. Am. Chem. Soc. 1987, 109, 4058 .
25. (a) Holmes, R. R.; Prakasha, T. K.; Pastor, S. D. In Phosphorus-31 NMR-Spectral Properties in Compound Characterization and Structural Analysis; Quin, L. D., Verkade, J. G., Eds.; VCH: New York, 1994; Chapter 3.
26. (b) Holmes, R. R.; Prakasha, T. K. Phosphorus, Sulfur, Silicon 1993, 80, 1 and references cited therein.
27. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon: Oxford, UK, 1986.
28. Said, M. A.; Kumara Swamy, K. C.; Veith, M.; Much, V. J. Chem. Soc., Perkin Trans. 1 1995, 2945.
29. Zwierzak, A. Can. J. Chem. 1954, 37, 1498.
30. Said, M. A.; Pülm, M.; Irmer, R. H.; Kumara Swamy, K. C. J. Am. Chem. Soc. 1996, 118, 9841.
31. Sheldrick, G. M. SHELXS-90. Acta Crystallogr. 1990, A46, 467.
32. Sheldrick, G. M. SHELXS-93, University of Göttingen, 1993.
33. Flack, H. D. Acta Crystallogr. 1983, A39, 876.
34. Chang, B. C.; Conrad, W. E.; Denney, D. B.; Denney, D. Z.; Edelman, R.; Powell, R. L.; White, D. W. J. Am. Chem. Soc. 1971, 93, 4004.
35. Sarma, R.; Ramirez, F.; Mckeever, B.; Marecek, J. F.; Lee, S. J. Am. Chem. Soc. 1976, 95, 581.
36. 20 by the oxidative addition of the quinone to the phosphite, see: Gallucci, J. C.; Holmes, R. R. Inorg. Chem. 1980, 19, 3540.
37. Said, M. A.; Kumara Swamy, K. C.; Chandra Mohan, K.; Venkata Lakshmi, N. Tetrahedron 1994, 50, 6989.
38. Timosheva, N. Y.; Prakasha, T. K.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1995, 34, 4525.
39. Huheey, J. E. Inorganic Chemistry, 3rd ed.; Harper International: Cambridge, UK, 1983; p 156.
40. Huang, Y.; Mullah, N. N.; Sopchik, A. E.; Arif, A. M.; Bentrude, W. G. Tetrahedron Lett. 1991, 32, 899.
41. Trippett, S. Pure Appl. Chem. 1974, 40, 595.
42. Holmes, R. R.; Day, R. O.; Deiters, J. A.; Kumara Swamy, K. C.; Holmes, J. M.; Hans, J.; Burton, S. D.; Prakasha, T. K. In Phosphorus Chemistry - Developments in American Science; (Walsh, E. N., Parry, R. W., Quin, L. D., Eds.; American Chemical Society: Washington, DC, 1992; Chapter 2.
43. (a) Arshinova, R. P. Russ. Chem. Rev. 1988, 57, 1142.
44. (b) Litvinov, I. A.; Struchkov, Yu. T.; Arbuzov, B. A.; Arshinova, R. P.; Ovodova, O. V. Zh. Strukt. Khim. 1984, 25, 118.
45. Kataeva, O. N.; Litvinov, I. A.; Naumov, V. A.; Mukmeneva, N. A. Zk. Strukt. Khim. 1989, 30, 166.
46. Elnagar, H. Y.; Layman, W. J.; Fronczek, F. R. Acta Crystallogr. 1995, C51, 1177.
47. (e) Pastor, S. D.; Shum, S. P.; Debellis, A. D.; Burke, L. P.; Rodenbaugh, R. K.; Clarke, F. H.; Rihs, G. Inorg. Chem. 1996, 55, 949.
48. Blom, R.; Haaland, A. J. Mol. Struct. 1985, 128, 21.
49. (a) Holmes, R. R.; Deiters, J. A. J. Am. Chem. Soc. 1977, 99, 3318.
50. (b) Spek, A. L. Acta Crystallogr. 1990, A46, C34.
51. Said, M. A.; Kumara Swamy, K. C.; Veith, M.; Huch, V. Inorg. Chem. 1996, 35, 6627.