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Updated: Dec 10, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

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A Stable Primary Phosphane Oxide and Its Heavier Congeners.

Filip Horký1, Ivana Císařová1, Petr Štěpnička1

  • 1Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40, Prague, Czech Republic.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 27, 2020
PubMed
Summary

The synthesis of primary phosphane chalcogenides, (ferrocenylmethyl)phosphane oxide, sulfide, and selenide, was achieved. These compounds exhibit unique reactivity, including tautomerization and addition reactions, offering new avenues in organophosphorus chemistry.

Keywords:
metallocenesphosphanesprimary phosphane chalcogenidesstructure elucidationsynthesis

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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Coordination Chemistry

Background:

  • Primary phosphanes are typically unstable and sterically hindered.
  • The synthesis and reactivity of phosphane chalcogenides are less explored.
  • Ferrocene-containing ligands offer unique electronic and steric properties.

Purpose of the Study:

  • To synthesize and characterize the first isolable primary phosphane chalcogenides.
  • To investigate the reactivity of these novel compounds with metal complexes and Lewis acids.
  • To explore the addition reactions of phosphane oxide with various unsaturated substrates.

Main Methods:

  • Oxidation of (ferrocenylmethyl)phosphane with H2O2, S, and Se.
  • Reactions with [(η6-mes)RuCl2]2 and B(C6F5)3.
  • Addition reactions with aldehydes, ketones, and cumulenes.

Main Results:

  • Isolation of (ferrocenylmethyl)phosphane oxide (1O), sulfide (1S), and selenide (1Se).
  • 1O undergoes tautomerization with ruthenium complexes and forms a Lewis pair with B(C6F5)3.
  • 1S and 1Se react with ruthenium complexes, losing their chalcogen atoms.
  • 1O adds to C=O and C=E bonds, with PH hydrogens participating in reactions with aldehydes and cyanates.

Conclusions:

  • The first sterically unprotected primary phosphane chalcogenides were synthesized.
  • These compounds display diverse reactivity, including tautomerization, chalcogen loss, and addition reactions.
  • The findings expand the scope of organophosphorus chemistry and coordination chemistry.