1,2,3,4-Heterohexatrienes as New Tools for Michael-Type Additions Usable for the Synthesis of Phosphorus Dendrimers

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

References

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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: [phone]; or [e-mail]].