Characterization of stereoisomers of spirophosphoranes bearing an eight- membered ring: Implications on apicophilicity in trigonal bipyramidal phosphorus [8]

Journal of the American Chemical Society

Volumn 122, Issue 5, 2000, Pages 964-965

  Kumaraswamy, Sudha ^a   Muthiah, C ^a   Kumara Swamy, K C ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORANE DERIVATIVE; PHOSPHORUS ACID DERIVATIVE;

ENANTIOMER; LETTER; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

EID: 0034624396     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992304v     Document Type: Letter

References (26)

1. Smith, D. J. H. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, V. D., Eds.; Vol. 2, Sutherland, I. O., Vol. Ed.; Pergamon: Exeter, 1979; pp 1233-1256.
2. Sheldrick, W. S. Top. Curr. Chem. 1978, 73, 1.
3. Trippett, S. Phosphorus Sulfur 1976, 1, 89.
4. Corbridge, D. E. C. Phosphorus: An Outline of its Chemistry, Biochemistry and Technology, 4th ed.; Eisevier: Amsterdam, 1990; Chapter 14, pp 994-1007.
5. (a) Schomburg, D.; Wermuth, U.; Schmutzler, R. Chem. Ber. 1987, 120, 1713.
6. (b) Kumara Swamy, K. C.; Holmes, J. M.; Day, R. O.; Holmes, R. R. J. Am. Chem. Soc. 1990, 112, 6092.
7. (c) Holmes, R. R.; Kumara Swamy, K. C.; Holmes, J. M.; Day, R. O. Inorg. Chem. 1991, 30, 1052.
8. (d) Prakasha, T. K.; Burton, S. D.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1992, 31, 5494.
9. Highly constrained ring systems are an exception: Huang, Y.; Arif, A. M.; Bentrude, W. G. J. Am. Chem. Soc. 1991, 113, 7800.
10. Kojima, S.; Kajiyama, K.; Nakamoto, M.; Akiba, K.-y. J. Am. Chem. Soc. 1996, 118, 12866.
11. (a) Kojima, S.; Kajiyama, K.; Akiba, K.-y. Tetrahedron Lett. 1994, 35, 7037.
12. (b) Kojima, S.; Nakamoto, M.; Akiba, K.-y. Tetrahedron Lett. 1995, 36, 2261.
13. (c) Kojima, S.; Kajiyama, K.; Akiba, K.-y. Bull. Chem. Soc. Jpn. 1995, 68, 1785.
14. (a) Said, M. A.; Pülm, M.; Herbst-Irmer, R.; Kumara Swamy, K. C. J. Am. Chem. Soc. 1996, 118, 9841.
15. (b) Said, M. A.; Pülm, M.; Herbst-Irmer, R.; Kumara Swamy, K. C. Inorg. Chem. 1997, 36, 3044.
16. For earlier studies, see: (a) Prakasha, T. K.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1995, 34, 1243. (b) Timosheva, N. Y.; Chandrasekaran, A.; Prakasha, T. K.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1996, 35, 6552.
17. For earlier studies, see: (a) Prakasha, T. K.; Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1995, 34, 1243. (b) Timosheva, N. Y.; Chandrasekaran, A.; Prakasha, T. K.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1996, 35, 6552.
18. Most of the compounds containing this ring have a tendency to crystallize well: (a) Said, M. A.; Kumara Swamy, K. C.; Veith, M.; Huch, V. J. Chem. Soc., Perkin Trans. 1 1995, 2945. (b) Said, M. A.; Kumara Swamy, K. C.; Chandra Mohan, K.; Venkata Lakshmi, N. Tetrahedron 1994, 50, 6989. Kumaraswamy, S.; Vijjulatha, M.; Muthiah, C.; Kumara Swamy, K. C.; Engelhardt, U. J. Chem. Soc., Dalton Trans. 1999, 891.
19. Most of the compounds containing this ring have a tendency to crystallize well: (a) Said, M. A.; Kumara Swamy, K. C.; Veith, M.; Huch, V. J. Chem. Soc., Perkin Trans. 1 1995, 2945. (b) Said, M. A.; Kumara Swamy, K. C.; Chandra Mohan, K.; Venkata Lakshmi, N. Tetrahedron 1994, 50, 6989. Kumaraswamy, S.; Vijjulatha, M.; Muthiah, C.; Kumara Swamy, K. C.; Engelhardt, U. J. Chem. Soc., Dalton Trans. 1999, 891.
20. Most of the compounds containing this ring have a tendency to crystallize well: (a) Said, M. A.; Kumara Swamy, K. C.; Veith, M.; Huch, V. J. Chem. Soc., Perkin Trans. 1 1995, 2945. (b) Said, M. A.; Kumara Swamy, K. C.; Chandra Mohan, K.; Venkata Lakshmi, N. Tetrahedron 1994, 50, 6989. Kumaraswamy, S.; Vijjulatha, M.; Muthiah, C.; Kumara Swamy, K. C.; Engelhardt, U. J. Chem. Soc., Dalton Trans. 1999, 891.
21. 2: C, 63.31; H, 5.09; N, 1.57. Found: C, 63.25; H. 5.12; N, 1.42.
22. X-ray data were collected on an Enraf-Nonius-MACH3 diffractometer at 293K using Mo Kα (λ = 0.71073 Å) radiation and capillary mounting. Structures were solved and refined using standard methods.
23. Sheldrick, G. M. SHELX-97; University of Göttingen, 1997.
24. Bergmann, D.; Hinze, J. In Struct. Bonding, 66, Electronegativity; Sen, K. D., Jørgensen, C. K., Eds.; Springer-Verlag: Heidelberg, 1987; pp 145-190.
25. Chandrasekaran, A.; Day, R. O.; Holmes, R. R. J. Am. Chem. Soc. 1997, 119, 11434.
26. 10