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

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

Guillaume Bousrez ¹ Emmanuel Nicolas ² Agathe Martinez ¹ Sylviane Chevreux ¹ Florian Jaroschik ¹

1 ICMR - Institut de Chimie Moléculaire de Reims - UMR 7312

2 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)

NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)

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.

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

Complete list of metadatas

Cited literature [43 references] Display Hide Download

https://hal-cea.archives-ouvertes.fr/cea-02092318
Contributor : Serge Palacin <>
Submitted on : Monday, April 8, 2019 - 8:30:32 AM
Last modification on : Wednesday, April 10, 2019 - 4:26:44 PM
Long-term archiving on: Wednesday, July 10, 2019 - 12:23:20 PM

HeteroatomChem_2596405.pdf

Publisher files allowed on an open archive

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

File

Identifiers

Collections

Citation

Export

Metrics

60

85

Contact

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

File

Identifiers

Collections

Citation

Export

Share

Metrics

60

85

Contact

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