Synthesis, structure, and thermolysis of pentacoordinate 1,3,2λ5- oxazaphosphetidines: The intermediates of aza-Wittig reactions

Tetrahedron Letters

Volumn 41, Issue 27, 2000, Pages 5237-5241

  Kano, Naokazu ^a   Hua, Xing Jia ^a   Kawa, Seiji ^a   Kawashima, Takayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aza Wittig reaction; Iminophosphorane; Oxazaphosphetidine; Thermolysis; X ray analysis

Indexed keywords

HETEROCYCLIC COMPOUND;

ARTICLE; CRYSTAL STRUCTURE; HEATING; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0343526417     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00829-7     Document Type: Article

References (24)

1. (a) Lukevics, E.; Pudova, O. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, U.K., 1996; Vol. 1B, pp. 1189-1213.
2. (b) Kawashima, T.; Okazaki, R. In Advances in Strained and Interesting Organic Molecules; Halton, B., Ed.; JAI Press: Stamford, Connecticut, 1999; Vol. 7, pp. 1-41.
3. (a) Kawashima, T.; Okazaki, R. Synlett 1996, 600-608, and references cited therein.
4. (b) Ohno, F.; Kawashima, T.; Okazaki, R. J. Am. Chem. Soc. 1996, 118, 697-698.
5. (c) Ohno, F.; Kawashima, T.; Okazaki, R. Chem. Commun. 1997, 1671-1672.
6. (a) Kawashima, T.; Kato, K.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 4008-4010.
7. (b) Kawashima, T.; Kato, K.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 869-870.
8. (c) Kawashima, T.; Kato, K.; Okazaki, R. Angew. Chem., Int. Ed. 1998, 37, 1606-1606.
9. (d) Kawashima, T.; Kato, K.; Okazaki, R. J. Am. Chem. Soc. 1998, 120, 6848-6848.
10. Kawashima, T.; Soda, T.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1096-1098.
11. For recent reviews on the aza-Wittig reaction, see: (a) Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406.
12. (b) Molina, P.; Vilaplana, M.J. Synthesis 1994, 1197-1218.
13. (a) Koketsu, J.; Ninomiya, Y.; Suzuki, Y.; Koga, N. Inorg. Chem. 1997, 36, 694-702.
14. (b) Lu, W. C.; Liu, C. B.; Sun, C. C. J. Phys. Chem. A. 1999, 103, 1078-1083.
15. Sheldrick, W. S.; Schomburg, D.; Schmidpeter, A.; Von Criegern, T. Chem. Ber. 1980, 113, 55-69.
16. (a) Storzer, W.; Röschenthaler, G.-V.; Schmutzler, R.; Sheldrick, W. S. Chem. Ber. 1981, 114, 3609-3624.
17. (b) Francke, R.; Dakternieks, D.; Gable, R. W.; Hoskins, B. F.; Röschenthaler, G.-V. Chem. Ber. 1985, 118, 922-930.
18. 2OLi, which can be prepared by directed lithiation of hexafluorocumyl alcohol, is usually used for the introduction of this ligand, see: Perozzi, E. F.; Michalak, R. S.; Figuly, G. D.; Stevenson III, W. H.; Dess, D. B.; Ross, M. R.; Martin, J. C. J. Org. Chem. 1981, 46, 1049-1053.
19. Cyclic phosphinite 5 gave the corresponding phosphinate 8 on exposure to air. Iminophosphorane 6 also gave readily 8 in the presence of water.
20. 2P: C, 53.80; H, 4.46; N, 2.09. Found: C, 54.03; H, 4.40; N, 1.91.
21. Granoth, I.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 4618-4621.
22. w)=0.043 (0.023).
23. Holmes, R. R.; Deiters, J. A. J. Am. Chem. Soc. 1977, 99, 3318-3326.
24. 19F NMR spectra of the reaction solution.