Synthesis and reactivity of 1-(2,4,6-trialkylphenyl) phospholes with a flattened p-pyramid

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Abstract

Due to their flattened P-pyramid, the title phospholes are of aromatic character and hence they undergo aromatic electrophilic substitution, such as Friedel-Crafts acylations. The arylphospholes were functionalized via the site-selective reaction with phosphorustribromide to provide substituted phospholes that are appropriate ligands in rhodium complexes used in hydroformylations. Despite their aromaticity, the arylphospholes take part in Diels-Alder reaction with dienophiles to result in the formation of phosphanorbornene derivatives useful in fragmentation related phosphorylations. At 150 °C, the 1Hphospholes were converted to the 2H-derivatives by a sigmatropic rearrangement to give, after trapping, 1- phosphanorbornadienes. The complexation and the oxidation reactions of the arylphospholes also revealed special features due to the presence of the trialkylphenyl substituent.

Original languageEnglish
Pages (from-to)245-269
Number of pages25
JournalTargets in Heterocyclic Systems
Volume6
Publication statusPublished - Jan 1 2002

ASJC Scopus subject areas

  • Analytical Chemistry
  • Process Chemistry and Technology
  • Organic Chemistry

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