1,2,3,4-Heterohexatrienes as new tools for Michael-type additions usable for the synthesis of phosphorus dendrimers

Synthesis

Volumn , Issue 3, 2003, Pages 389-396

  Maraval, Valérie ^a   Laurent, Régis ^a   Donnadieu, Bruno ^a   Caminade, Anne Marie ^a   Majoral, Jean Pierre ^a  

^a CNRS   (France)

Author keywords

Alkenes; Aminations; Dendrimers; Michael additions; Phosphorus

Indexed keywords

ADDITION REACTIONS; AMINES; CONDENSATION; SYNTHESIS (CHEMICAL);

FUNCTIONALIZED AMINES;

DENDRIMERS;

1,2,3,4 HETEROHEXATRIENE; ALKENE; AMINE; DENDRIMER; HYDRAZINE; IMIDAZOLE; PHENOL; PHOSPHORUS; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CRYSTALLOGRAPHY; MICHAEL ADDITION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037235028     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37356     Document Type: Article

References (26)

1. See for instance: Bernasconi, C. F. Tetrahedron 1989, 45, 4017; and references included therein.
2. See for instance: (a) Märkl, G.; Merkl, B. Tetrahedron Lett. 1981, 22, 4459. (b) Pietrusiewicz, K. M.; Zablocka, M. Tetrahedron Lett. 1988, 29, 1991. (c) Märkl, G.; Merkl, B. Tetrahedron Lett. 1981, 22, 4463. (d) Pietrusiewicz, K. M.; Zablocka, M. Phosphorus, Sulfur Silicon Relat. Elem. 1988, 40, 47.
3. See for instance: (a) Märkl, G.; Merkl, B. Tetrahedron Lett. 1981, 22, 4459. (b) Pietrusiewicz, K. M.; Zablocka, M. Tetrahedron Lett. 1988, 29, 1991. (c) Märkl, G.; Merkl, B. Tetrahedron Lett. 1981, 22, 4463. (d) Pietrusiewicz, K. M.; Zablocka, M. Phosphorus, Sulfur Silicon Relat. Elem. 1988, 40, 47.
4. See for instance: (a) Märkl, G.; Merkl, B. Tetrahedron Lett. 1981, 22, 4459. (b) Pietrusiewicz, K. M.; Zablocka, M. Tetrahedron Lett. 1988, 29, 1991. (c) Märkl, G.; Merkl, B. Tetrahedron Lett. 1981, 22, 4463. (d) Pietrusiewicz, K. M.; Zablocka, M. Phosphorus, Sulfur Silicon Relat. Elem. 1988, 40, 47.
5. See for instance: (a) Märkl, G.; Merkl, B. Tetrahedron Lett. 1981, 22, 4459. (b) Pietrusiewicz, K. M.; Zablocka, M. Tetrahedron Lett. 1988, 29, 1991. (c) Märkl, G.; Merkl, B. Tetrahedron Lett. 1981, 22, 4463. (d) Pietrusiewicz, K. M.; Zablocka, M. Phosphorus, Sulfur Silicon Relat. Elem. 1988, 40, 47.
6. Maraval, V.; Laurent, R.; Donnadieu, B.; Mauzac, M.; Caminade, A. M.; Majoral, J. P. J. Am Chem. Soc. 2000, 122, 2499.
7. Maraval, V.; Sebastian, R. M.; Ben, F.; Laurent, R.; Caminade, A. M.; Majoral, J. P. Eur. J. Inorg. Chem. 2001, 1681.
8. Maraval, V.; Laurent, R.; Merino, S.; Caminade, A. M.; Majoral, J. P. Eur. J. Org. Chem. 2000, 3555.
9. Majoral, J. P.; Caminade, A. M. Chem. Rev. 1999, 99, 845.
10. (a) Galliot, C.; Larré, C.; Caminade, A. M.; Majoral, J. P. Science 1997, 277, 1981
11. (b) Larré, C.; Caminade, A. M.; Majoral, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 596.
12. (c) Larré, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. J. Am. Chem. Soc. 1998, 120, 4029.
13. (d) Larré, C.; Bressolles, D.; Turrin, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. J. Am. Chem. Soc. 1998, 120, 13070.
14. (e) Majoral, J. P.; Larré, C.; Laurent, R.; Caminade, A. M. Coord. Chem. Rev. 1999, 190-192, 3.
15. Traetteberg, M. Acta Chem. Scand. 1968, 22, 628.
16. (a) Allcock, H. R.; Tollefson, N. M.; Arcus, R. A.; Whittle, R. R. J. Am Chem. Soc. 1985, 107, 5166.
17. (b) Bougeard, D.; Brémard, C.; de Jaeger, R.; Lemmouchi, Y. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 79, 147.
18. CCDC 197221 for 1 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk].
19. Turrin, C. O.; Maraval, V.; Caminade, A. M.; Majoral, J. P.; Mehdi, A.; Reyé, C. Chem. Mat. 2000, 12, 3848.
20. Alijarin, M.; Lopez-Leonardo, C.; Llamas-Lorente, P. Tetrahedron Lett. 2001, 42, 605.
21. (a) SIR92 - A Program for Crystal Structure Solution: Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Crystallogr. 1993, 26, 343.
22. (b) SIR97: Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Cryst. 1999, 32, 115.
23. SHELX97 (Includes SHELXS97, SHELXL97, CIFTAB) - Programs for Crystal Structure Analysis (Release 97-2); Sheldrick, G. M., Ed.; Institüt für Anorganische Chemie der Universität: Göttingen, Germany, 1998.
24. WINGX - 1.63 Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-Ray Diffraction Data: Farrugia, L. J. Appl. Crystallogr. 1999, 32, 837.
25. International Tables for X-Ray Crystallography, Vol IV; Kynoch Press: Birmingham England, 1974.
26. ORTEP32 for Windows: Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.