Center-to-propeller and propeller-to-propeller stereocontrol in a series of macrobicyclic tri-λ5-phosphazenes

Tetrahedron Letters

Volumn 48, Issue 20, 2007, Pages 3583-3586

  Alajarín, Mateo ^a   López Leonardo, Carmen ^a   Berná, José ^a   Sánchez Andrada, Pilar ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

Cage compounds; Propeller macrobicycles

Indexed keywords

AMINE; BENZYL DERIVATIVE; BICYCLO COMPOUND; PHOSPHORUS DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONFORMATION; DIASTEREOISOMER; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; STEREOCHEMISTRY;

EID: 34247165783     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.087     Document Type: Article

References (24)

1. Alajarín M., Vidal A., López-Leonardo C., Berná J., and Ramírez de Arellano M.C. Tetrahedron Lett. 39 (1998) 7807
2. Alajarín M., López-Leonardo C., and Berná J. Tetrahedron 62 (2006) 6190
3. Staudinger H., and Meyer J. Helv. Chim. Acta 2 (1919) 635
4. Gololobov Y.G., Zhmurova I.N., and Kasukhin L.F. Tetrahedron 37 (1981) 437
5. Gololobov Y.G., and Kasukhin L.F. Tetrahedron 48 (1992) 1353
6. Johnson A.W. Ylides and Imines of Phosphorus (1993), Wiley, New York p 403
7. Alajarín M., López-Leonardo C., Vidal A., Berná J., and Steed J.W. Angew. Chem., Int. Ed. 41 (2002) 1205
8. Comparable situations have been found in:. McIntosh J.M. J. Org. Chem. 47 (1982) 3777
9. Canary J.W., Allen C.S., Castagnetto J.M., and Wang Y. J. Am. Chem. 117 (1995) 8484
10. Canary J.W., Allen C.S., Castagnetto J.M., Chiu Yu.-H., Toscano P.J., and Wang Y. Inorg. Chem. 37 (1998) 6255
11. Chiu Y.-H., Dos Santos O., and Canary J.W. Tetrahedron 55 (1999) 12069
12. Zahn S., Das D., and Canary J.W. Inorg. Chem. 45 (2005) 6056
13. Merrill, S. H.; Unruh, C. C. U.S. Patent 3,002,003, 1959.
14. Merrill S.H., and Unruh C.C. Chem. Abstr. 56 (1962) 4961i
15. Fort G., and McLean A. J. Am. Chem. Soc. (1948) 1902
16. Latour S., and Wuest J.D. Synthesis (1987) 742
17. Janssen B.C., Asam A., Huttner G., Sernau V., and Zsolnai L. Chem. Ber. 127 (1994) 501
18. Ott J., Venanzi L.M., Ghilardi C.A., Midollini S., and Orlandini A. J. Organomet. Chem. 291 (1985) 89
19. Tris(phosphanes) 3d and 3e were prepared following the same experimental procedure used for 3c, as reported in Ref. 8.
20. 3J(C,P) = 12.7 Hz;s-cis-CH{double bond, long}C-N{double bond, long}P), 123.99
21. Wolinski K., Hinton J.F., and Pulay P. J. Am. Chem. Soc. 112 (1990) 8251
22. Cheeseman J.R., Trucks G.W., Keth T., and Frisch M.J. J. Chem. Phys. 104 (1996) 5497
23. Helgaker T., Jaszunski M., and Ruud K. Chem. Rev. 99 (1999) 293
24. + force field as implemented in the HyperChem 6.0 molecular modeling program (Hypercube, Inc; http://www.hyper.com).