%0 Journal Article %T [​4+2] versus [​2+2] Homodimerization in P(V) Derivatives of 2,4-Disubstituted Phospholes %+ Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR) %+ Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF) (LCMCE) %A Bousrez, Guillaume %A Nicolas, Emmanuel %A Martinez, Agathe %A Chevreux, Sylviane %A Jaroschik, Florian %< avec comité de lecture %@ 1042-7163 %J Heteroatom Chemistry %I Wiley %V 2019 %P 2596405 %8 2019-04-01 %D 2019 %R 10.1155/2019/2596405 %Z Chemical Sciences/Organic chemistryJournal articles %X 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. %G English %2 https://cea.hal.science/cea-02092318/document %2 https://cea.hal.science/cea-02092318/file/HeteroatomChem_2596405.pdf %L cea-02092318 %U https://cea.hal.science/cea-02092318 %~ CEA %~ CNRS %~ URCA %~ PUBNIMBE %~ DSV %~ INC-CNRS %~ IRAMIS-NIMBE %~ CEA-UPSAY %~ UNIV-PARIS-SACLAY %~ CEA-UPSAY-SACLAY %~ ICMR %~ CEA-DRF %~ ICMRCC %~ ICMRMSO %~ TEST-HALCNRS %~ GS-ENGINEERING %~ IRAMIS %~ GS-CHIMIE %~ GS-PHYSIQUE %~ INSTITUT-SCIENCES-LUMIERE %~ TEST2-HALCNRS