Template synthesis of the first 1,4,7-triphosphacyclononane derivatives

Angewandte Chemie - International Edition

Volumn 39, Issue 16, 2000, Pages 2922-2924

  Edwards, Peter G ^a   Newman, Paul D ^a   Malik, K M Abdul ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

Cyclizations; Iron; Macrocycles; Phosphorus heterocycles; Template synthesis

Indexed keywords

1,4,7 TRIAZACYCLONONANE; 1,4,7 TRITHIACYCLONONANE; ACETONITRILE; LIGAND; UNCLASSIFIED DRUG;

ARTICLE; LIGAND BINDING; METHODOLOGY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034683049     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000818)39:16<2922::AID-ANIE2922>3.0.CO;2-S     Document Type: Article

References (21)

1. Fora recent extensive review see: I. A. Fallis, Annu. Rep. Prog. Chem. Sect. A 1999, 95, 313.
2. E. P. Kyba, R. E. Liu, S.-T. Davis, K. A. Hasset, S. B. Larson, Inorg. Chem. 1985, 24, 4629, and references therein.
3. B. N. Diel, P.F. Brandt, R. C. Haltiwanger, L. J. Hackney, A. D. Norman, Inorg. Chem. 1989, 28, 2811.
4. a) P. G. Edwards, J. S. Fleming, S. S. Liyanage, Inorg. Chem. 1996, 35, 4563;
5. b) P. G. Edwards, D. J. Jones, R.P Tooze, T. Albers, J. Chem. Soc. Dalton Trans. 1999, 1045 and references therein.
6. P. G. Edwards, J. S. Fleming, S.S. Liyanage, S. J. Coles, M. B. Hursthouse, J. Chem. Soc. Dalton Trans. 1996, 1801.
7. a) G. T. Crisp. G. Salem, S. B. Wild, Organnmetallics 1989, 8, 2360:
8. b) A. Bader, Y. B. Kang, M. Pabel, D. D. Pathak, A. C. Willis, S. B. Wild, Organometallics 1995, 14, 1434.
9. D. Catheline, D. Astruc, Organometallics 1984, 3, 1094.
10. 13C NMR of Transition Metal Complexes, Springer, Berlin, 1979.
11. cq of the parent atoms. The ethyl carbon atom C17 was disordered but satisfactorily refined in two positions with 50% occupancies; hydrogen atoms on C17 were ignored. The disorder model clearly indicates rotational freedom of the ethyl group; both positions giving realistic molecular conformations and only one is displayed in Figure 1. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-142396. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk). We thank Dr. M. Thornton-Pett of Leeds University (UK) for the data collection.
12. R. Hooft, COLLECT data collection software, Nonius B. V., Delft, The Netherlands, 1998.
13. Z. Otwinowski, W. Minor in Macromolecular Crystallography, (Eds.: C.W. Carter, Jr., R. M. Sweet). Academic Press, New York, 1997, pp. 307-326.
14. S. Mackay, C.J. Gilmore, C. Edwards, M. Tremayne, N. Stuart, K. Shankland. maXus program for the solution of structures from diffraction data, University of Glasgow, Scotland, UK, 1998.
15. G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467.
16. G. M. Sheldrick, SHELX-93, program for crystal structure refinement, University of Gottingen, Germany, 1996.
17. L. J. Farrugia, Ortep for Windows version 1.0, University of Glasgow, 1997. Note added in proof: During publication of this manuscript we also reported on a similar iron template mediated macrocyclization of 1,2-arylene biphosphane precursors ("A New Nine-Membered Triphosphorus Macrocycle", Organometallics 2000, 19, 2652) ; this paper dealt with the formation of a rigid ring system related to the larger eleven-membered macrocycles previously described by Kyba and co-workers (see, for example: E. P. Kyba, R. E. Davies, S.-T. Liu, K. A. Hasset, S. B. Larsen, Inorg. Chem. 1985, 24, 4629). In view of the rigidity of the chelating 1,2-arylene biphosphane functionality in these macrocycles, they may be expected to offer substantially different coordination properties than the parent aliphatic ring system reported for the first time herein; they would also be expected to be electronically distinct. Indeed, the versatility of the new template methodology described is emphasized by the opportunity to introduce stereochemical control, which in turn enables synthetic routes to alternative macrocyclic structures and supports unprecedented ring-closure reactions. These observations are exemplified in our recent discussion of the formation of chiral. intermediate ring sizes (Angew. Chem. 2000, 112, 2834; Angew. Chem. Int. Ed. 2000, 39, 2722). Our oversight in not cross-referencing the three articles is partly corrected through this note, added in proof upon the request of the editor.
18. L. J. Farrugia, Ortep for Windows version 1.0, University of Glasgow, 1997. Note added in proof: During publication of this manuscript we also reported on a similar iron template mediated macrocyclization of 1,2-arylene biphosphane precursors ("A New Nine-Membered Triphosphorus Macrocycle", Organometallics 2000, 19, 2652) ; this paper dealt with the formation of a rigid ring system related to the larger eleven-membered macrocycles previously described by Kyba and co-workers (see, for example: E. P. Kyba, R. E. Davies, S.-T. Liu, K. A. Hasset, S. B. Larsen, Inorg. Chem. 1985, 24, 4629). In view of the rigidity of the chelating 1,2-arylene biphosphane functionality in these macrocycles, they may be expected to offer substantially different coordination properties than the parent aliphatic ring system reported for the first time herein; they would also be expected to be electronically distinct. Indeed, the versatility of the new template methodology described is emphasized by the opportunity to introduce stereochemical control, which in turn enables synthetic routes to alternative macrocyclic structures and supports unprecedented ring-closure reactions. These observations are exemplified in our recent discussion of the formation of chiral. intermediate ring sizes (Angew. Chem. 2000, 112, 2834; Angew. Chem. Int. Ed. 2000, 39, 2722). Our oversight in not cross-referencing the three articles is partly corrected through this note, added in proof upon the request of the editor.
19. L. J. Farrugia, Ortep for Windows version 1.0, University of Glasgow, 1997. Note added in proof: During publication of this manuscript we also reported on a similar iron template mediated macrocyclization of 1,2-arylene biphosphane precursors ("A New Nine-Membered Triphosphorus Macrocycle", Organometallics 2000, 19, 2652) ; this paper dealt with the formation of a rigid ring system related to the larger eleven-membered macrocycles previously described by Kyba and co-workers (see, for example: E. P. Kyba, R. E. Davies, S.-T. Liu, K. A. Hasset, S. B. Larsen, Inorg. Chem. 1985, 24, 4629). In view of the rigidity of the chelating 1,2-arylene biphosphane functionality in these macrocycles, they may be expected to offer substantially different coordination properties than the parent aliphatic ring system reported for the first time herein; they would also be expected to be electronically distinct. Indeed, the versatility of the new template methodology described is emphasized by the opportunity to introduce stereochemical control, which in turn enables synthetic routes to alternative macrocyclic structures and supports unprecedented ring-closure reactions. These observations are exemplified in our recent discussion of the formation of chiral. intermediate ring sizes (Angew. Chem. 2000, 112, 2834; Angew. Chem. Int. Ed. 2000, 39, 2722). Our oversight in not cross-referencing the three articles is partly corrected through this note, added in proof upon the request of the editor.
20. L. J. Farrugia, Ortep for Windows version 1.0, University of Glasgow, 1997. Note added in proof: During publication of this manuscript we also reported on a similar iron template mediated macrocyclization of 1,2-arylene biphosphane precursors ("A New Nine-Membered Triphosphorus Macrocycle", Organometallics 2000, 19, 2652) ; this paper dealt with the formation of a rigid ring system related to the larger eleven-membered macrocycles previously described by Kyba and co-workers (see, for example: E. P. Kyba, R. E. Davies, S.-T. Liu, K. A. Hasset, S. B. Larsen, Inorg. Chem. 1985, 24, 4629). In view of the rigidity of the chelating 1,2-arylene biphosphane functionality in these macrocycles, they may be expected to offer substantially different coordination properties than the parent aliphatic ring system reported for the first time herein; they would also be expected to be electronically distinct. Indeed, the versatility of the new template methodology described is emphasized by the opportunity to introduce stereochemical control, which in turn enables synthetic routes to alternative macrocyclic structures and supports unprecedented ring-closure reactions. These observations are exemplified in our recent discussion of the formation of chiral. intermediate ring sizes (Angew. Chem. 2000, 112, 2834; Angew. Chem. Int. Ed. 2000, 39, 2722). Our oversight in not cross-referencing the three articles is partly corrected through this note, added in proof upon the request of the editor.
21. L. J. Farrugia, Ortep for Windows version 1.0, University of Glasgow, 1997. Note added in proof: During publication of this manuscript we also reported on a similar iron template mediated macrocyclization of 1,2-arylene biphosphane precursors ("A New Nine-Membered Triphosphorus Macrocycle", Organometallics 2000, 19, 2652) ; this paper dealt with the formation of a rigid ring system related to the larger eleven-membered macrocycles previously described by Kyba and co-workers (see, for example: E. P. Kyba, R. E. Davies, S.-T. Liu, K. A. Hasset, S. B. Larsen, Inorg. Chem. 1985, 24, 4629). In view of the rigidity of the chelating 1,2-arylene biphosphane functionality in these macrocycles, they may be expected to offer substantially different coordination properties than the parent aliphatic ring system reported for the first time herein; they would also be expected to be electronically distinct. Indeed, the versatility of the new template methodology described is emphasized by the opportunity to introduce stereochemical control, which in turn enables synthetic routes to alternative macrocyclic structures and supports unprecedented ring-closure reactions. These observations are exemplified in our recent discussion of the formation of chiral. intermediate ring sizes (Angew. Chem. 2000, 112, 2834; Angew. Chem. Int. Ed. 2000, 39, 2722). Our oversight in not cross-referencing the three articles is partly corrected through this note, added in proof upon the request of the editor.