Macrobicyclic triphosphazides and tri-λ5-phosphazenes derived from PhC(CH2PPh2)3. Two propeller-shaped diastereoisomers in the crystals

Tetrahedron

Volumn 63, Issue 9, 2007, Pages 2078-2083

  Alajarín, Mateo ^a   López Leonardo, Carmen ^a   Berná, José ^a   Steed, Jonathan W ^b  

^a UNIVERSITY OF MURCIA   (Spain)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

Cage compound; Macrobicycle; Propeller; Tri 5 phosphazene; Triphosphazide; Tripod tripod coupling

Indexed keywords

ALKENE DERIVATIVE; AZIDE; BICYCLO COMPOUND; CHLOROFORM; PHOSPHORUS DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIASTEREOISOMER; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; SOLID STATE; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 33846388457     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.027     Document Type: Article

References (29)

1. Alajarín M., Molina P., López-Lázaro A., and Foces-Foces C. Angew. Chem., Int. Ed. 36 (1997) 67
2. Alajarín M., López-Lázaro A., Vidal A., and Berná J. Chem.-Eur. J. 4 (1998) 2558
3. Alajarín M., Vidal A., López-Leonardo C., Berná J., and Ramírez de Arellano M.C. Tetrahedron Lett. 39 (1998) 7807
4. Alajarín M., López-Leonardo C., Vidal A., Berná J., and Steed J.W. Angew. Chem., Int. Ed. 41 (2002) 1205
5. Alajarín M., López-Leonardo C., and Berná J. Tetrahedron 62 (2006) 6190
6. Lehn J.M. Supramolecular Chemistry: Concepts and Perspectives (1995), VCH, New York, NY p 140
7. Steed J.W., and Atwood J.L. Supramolecular Chemistry (2000), Wiley, New York, NY p 461
8. Staudinger H., and Meyer J. Helv. Chim. Acta 2 (1919) 635
9. Gololobov Y.G., Zhmurova I.N., and Kasukhin L.F. Tetrahedron 37 (1981) 437
10. Gololobov Y.G., and Kasukhin L.F. Tetrahedron 48 (1992) 1353
11. Johnson A.W. Ylides and Imines of Phosphorus (1993), Wiley, New York, NY p 403
12. Kim D.H., Park J.H., and Cho S.D. J. Korean Chem. Soc. 36 (1992) 163
13. Chem. Abstr. 116 (1992) 142759
14. Viguier R., Seratrice G., Dupraz A., and Dupuy C. Eur. J. Inorg. Chem. (2001) 1789
15. Alajarín M., Conesa C., and Rzepa H.S. J. Chem. Soc., Perkin Trans. 2 (1999) 1811
16. Widauer C., Grützmacher H., Shevchenko Y., and Gramlich V. Eur. J. Inorg. Chem. (1999) 1659
17. For examples of phosphazides that equilibrate in solution with their phosphane and azide counterparts, see:
18. Leffler J.E., Honsberg U., Tsuno Y., and Forsblad I. J. Org. Chem. 26 (1961) 4810
19. Leffler J.E., and Tsuno Y. J. Org. Chem. 28 (1963) 902
20. Leffler J.E., and Temple R.D. J. Am. Chem. Soc. 89 (1967) 5235
21. The conventional assignment of the stereochemical descriptor P or M (helical twist sense) to the propeller units of the chiral macrobicycles was made by looking at the molecule along its three-fold axis from the side of the tribenzylamine fragment.
22. -1. Detailed X-ray crystallographic data can be obtained, free of charge, on application to Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/data_request/cif. (CCDC No. 613199).
23. Semiempirical calculations were carried out using the MNDO method as implemented in the Gaussian 98 set of programs. The geometries of both stationary points were optimized, and harmonic frequency calculations were performed in order to characterize both structures as minima.
24. csqrt(2)/πΔν)) following:. Williams D.H., and Fleming I. Spectroscopic Methods in Organic Chemistry. 4th ed. (1989), McGraw-Hill, New York, NY p 103
25. For some recent examples see:
26. Vickaryous W.J., Herges R., and Johnson D.W. Angew. Chem., Int. Ed. 43 (2004) 5831
27. Rudzevich Y., Rudzevich V., Schollmeyer D., Thondorf I., and Böhmer V. Org. Lett. 7 (2005) 613
28. Bonnot C., Chambron J.-C., and Espinosa E. J. Am. Chem. Soc. 126 (2004) 11412
29. Alajarín M., Pastor A., Orenes R.A., Steed J.W., and Arakawa R. Chem.-Eur. J. 10 (2004) 1383