Phosphole

  Phosphole is the organic compound with the chemical formula C₄H₄PH; it is the phosphorus analog of pyrrole. The term phosphole also refers to substituted derivatives of the parent heterocycle. These compounds are of theoretical interest but also serve as ligands for transition metals and as precursors to more complex organophosphorus compounds.

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The first phosphole was discovered in 1953, pentaphenylphosphole followed in 1959 and the parent compound, phosphole itself, was first synthesized in 1987 ^[1]. Phenylphospholes can be prepared via treatment of a organozirconium compound with PhPCl₂.^[2]

Unlike other the 5-membered heterocycles pyrrole, thiophene, and furan, the aromaticity of phospholes is diminished, reflecting the reluctance of phosphorus to delocalize its lone pair.^[3] For example, phospholes undergo Diels-Alder reactions with electrophilic alkynes.

See also

• Organophosphorus chemistry
• Phosphorine

References