[​4+2] versus [​2+2] Homodimerization in P(V) Derivatives of 2,4-Disubstituted Phospholes

Abstract : Phosphole P(V) derivatives are interesting building blocks for various applications from ligand synthesis to material sciences. We herein describe the preparation and characterisation of new 2,4-disubstituted oxo-, thiooxo-, and selenooxophospholes. The nature of the substituents on the phosphole ring determines the reactivity of these compounds towards homodimerization reactions. Aryl and trimethylsilyl substituted oxophospholes undergo selective [4+2] dimerization, whereas, for thiooxo-and selenooxophospholes, light-induced, selective [2+2] head-to-head dimerization occurs in the case of aryl substituents. DFT calculations provide some insights on these differences in reactivity.
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Guillaume Bousrez, Emmanuel Nicolas, Agathe Martinez, Sylviane Chevreux, Florian Jaroschik. [​4+2] versus [​2+2] Homodimerization in P(V) Derivatives of 2,4-Disubstituted Phospholes. Heteroatom Chemistry, Wiley, 2019, 2019, pp.2596405. ⟨https://www.hindawi.com/journals/htrc/2019/2596405/⟩. ⟨10.1155/2019/2596405⟩. ⟨cea-02092318⟩

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