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DOI: 10.1055/s-2003-37356
1,2,3,4-Heterohexatrienes as New Tools for Michael-Type Additions Usable for the Synthesis of Phosphorus Dendrimers
Publication History
Publication Date:
19 February 2003 (online)
Abstract
Linear 1,2,3,4-heterohexatrienes of type H2C=CHP(R)2=NP(R′)2=X (X = O, S) are used in Michael-type additions of various primary or secondary amines and hydrazines. The use of functionalized amines allowed the grafting of other functions, such as a double or a triple bond, a sulfide, an imidazole, or a phenol, and various types of NH2 groups. These groups were used in condensation reactions, leading to the grafting of new functions such as phenols. Thus, the P(R)2=NP(R′)2=X group appears as a new electron withdrawing group, very easily tunable by changing the R′ or X substituents.
Key words
Michael additions - alkenes - aminations - dendrimers - phosphorus
- 1 See for instance:
Bernasconi CF. Tetrahedron 1989, 45: 4017 ; and references included therein - See for instance:
- 2a
Märkl G.Merkl B. Tetrahedron Lett. 1981, 22: 4459 - 2b
Pietrusiewicz KM.Zablocka M. Tetrahedron Lett. 1988, 29: 1991 - 2c
Märkl G.Merkl B. Tetrahedron Lett. 1981, 22: 4463 - 2d
Pietrusiewicz KM.Zablocka M. Phosphorus, Sulfur Silicon Relat. Elem. 1988, 40: 47 - 3
Maraval V.Laurent R.Donnadieu B.Mauzac M.Caminade AM.Majoral JP. J. Am Chem. Soc. 2000, 122: 2499 - 4
Maraval V.Sebastian RM.Ben F.Laurent R.Caminade AM.Majoral JP. Eur. J. Inorg. Chem. 2001, 1681 - 5
Maraval V.Laurent R.Merino S.Caminade AM.Majoral JP. Eur. J. Org. Chem. 2000, 3555 - 6
Majoral JP.Caminade AM. Chem. Rev. 1999, 99: 845 - 7a
Galliot C.Larré C.Caminade AM.Majoral JP. Science 1997, 277: 1981 - 7b
Larré C.Caminade AM.Majoral JP. Angew. Chem., Int. Ed. Engl. 1997, 36: 596 - 7c
Larré C.Donnadieu B.Caminade AM.Majoral JP. J. Am. Chem. Soc. 1998, 120: 4029 - 7d
Larré C.Bressolles D.Turrin C.Donnadieu B.Caminade AM.Majoral JP. J. Am. Chem. Soc. 1998, 120: 13070 - 7e
Majoral JP.Larré C.Laurent R.Caminade AM. Coord. Chem. Rev. 1999, 190-192: 3 - 8
Traetteberg M. Acta Chem. Scand. 1968, 22: 628 - 9a
Allcock HR.Tollefson NM.Arcus RA.Whittle RR. J. Am Chem. Soc. 1985, 107: 5166 - 9b
Bougeard D.Brémard C.de Jaeger R.Lemmouchi Y. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 79: 147 - 11
Turrin CO.Maraval V.Caminade AM.Majoral JP.Mehdi A.Reyé C. Chem. Mat. 2000, 12: 3848 - 12
Alijarin M.Lopez-Leonardo C.Llamas-Lorente P. Tetrahedron Lett. 2001, 42: 605 - 13a SIR92
- A Program for Crystal Structure Solution:
Altomare A.Cascarano G.Giacovazzo C.Guagliardi A. J. Appl. Crystallogr. 1993, 26: 343 - 13b SIR97:
Altomare A.Burla MC.Camalli M.Cascarano GL.Giacovazzo C.Guagliardi A.Moliterni AGG.Polidori G.Spagna R. J. Appl. Cryst. 1999, 32: 115 - 14
SHELX97 (Includes SHELXS97,
SHELXL97, CIFTAB) - Programs for Crystal Structure
Analysis (Release 97-2)
Sheldrick GM. Institüt für Anorganische Chemie der Universität; Göttingen, Germany: 1998.Reference Ris Wihthout Link - 15 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 - 16
International Tables for
X-Ray Crystallography
Vol IV:
Kynoch Press;
Birmingham
England:
1974.
Reference Ris Wihthout Link
- 17 ORTEP32 for Windows:
Farrugia LJ. J. Appl. Crystallogr. 1997, 30: 565
References
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].