Reactivity of carbon anions α to pentacoordinated phosphorus: Spirooxyphosphoranyl C-anions as valuable intermediates in olefination chemistry

Journal of the American Chemical Society

Volumn 118, Issue 6, 1996, Pages 1549-1550

  Bojin, Mihaela L ^a   Barkallah, Salim ^a   Evans Jr , Slayton A ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE;

ALKYLATION; ARTICLE; CHIRALITY; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0029966055     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952095o     Document Type: Article

References (31)

1. Swamy, K. C. K.; Burton, S. D.; Holmes, J. M.; Day, R. O.; Holmes, R. R. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 53, 437-455.
2. Koenig, M.; Munoz, A., Garrigues, B. Wolf, R. Phosphorus Sulfur Relat. Elem. 1979, 6, 435.
3. Unpublished results with Powers, T. A., Bojin, M. L., and McKithen, M., University of North Carolina, Chapel Hill, NC.
4. (a) Holmes, R. R. In Pentacoordinated Phosphorus, Vol. 1. Structure and Spectroscopy; ACS Monograph 175: American Chemical Society: Washington, DC, 1980.
5. (b) Well, M.; Albers, W.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 801-808.
6. For an alternative view, e.g., equatoriphilicity and stabilization of the equatorial plane of the phosphorane as the major determinant for conformational preference, see: Wasade, H.; Hirao, K. J. Am. Chem. Soc. 1992, 114, 16.
7. Berry, R. S. J. Chem. Phys. 1960, 32, 933.
8. Ramirez, F.; Ugi, I. Adv. Phys. Org. Chem. 1971, 9, 256.
9. (a) Bestman, H. J.; Kos, A. J.; Witzgall, K.; Schleyer, P. v. R. Chem. Ber. 1986, 1331.
10. (b) Magnusson, E. J. Am. Chem. Soc. 1990, 112, 7940.
11. Reed A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434.
12. 5-phosphetanes 11a,b have been reported. (Formula Presented)
13. (b) Kawashima, T.; Kato, K.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 869.
14. (c) Kawashima, T.; Kato, K.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 4008.
15. (d) Kawashima, T., Iwama, N.; Okazaki, R. Ibid. 1992 114, 7598.
16. (a) Lamande, L.; Munoz, A. Phosphorus Sulfur Relat. Elem. 1987, 32, 1.
17. (b) Lamande, L.; Munoz, A. Tetrahedron 1990, 46, 3527-3534.
18. (a) Munoz, A.; Lamande, L. Phosphorus. Sulfur Silicon Relat. Elem. 1990, 49/50, 373-376.
19. (b) Munoz, A.; Lamande, L. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 70, 263-272.
20. PC = 8.55 Hz).
21. (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
22. (b) Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1.
23. Asahi Research Center. Handbook of Proton-NMR Spectra and Data, Academic Press: Tokyo, 1985; Vol. 4, p 43.
24. Chassaing, G.; Marquet, A. Tetrahedron 1978, 34, 1399.
25. (a) Sdeyden-Penne, J. Bull. Soc. Chim. Fr. 1988 (11), 238-242.
26. (b) Strzalko, T.; Seyden-Penne, J.; Froment, F.; Corset, J.; Simonnin, M.-P. Can. J. Chem. 1988, 66, 391-396.
27. (c) Corset, J. Pure Appl. Chem. 1986, 58, 1133-1146.
28. (a) Font Freide, J. J. H. M.; Trippett, S. J. Chem. Soc., Chem. Commun. 1980, 157.
29. (b) Denney, D. B.; Denney, D. Z.; Hammond, P. J.; Wang, Y. P.; Liu, L. T. J. Am. Chem. Soc. 1981, 103, 1785.
30. For an overview of a MNDO-PM3 treatment of transition states for Wittig half-reactions, see, for example: Mari, F.; Lahti, P. M.; McEwen, W. E. J. Am. Chem. Soc. 1992, 114, 813.
31. Larsen, R. O.; Aksnes, G. Phosphorus Sulfur Relat. Elem. 1983, 16, 339-344.