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Phospholenes from Phosphabenzenes by Selective Ring Contraction.

Jinxiong Lin1, Nathan T Coles1,2, Lea Dettling1

  • 1Freie Universität Berlin, Institut für Chemie und Biochemie, Fabeckstrasse 34/36, 14195, Berlin, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 16, 2022
PubMed
Summary
This summary is machine-generated.

A novel amino-phosphabenzene was synthesized. This compound undergoes a unique ring contraction in water, forming a hydroxylphospholene oxide, unlike related pyridine compounds.

Keywords:
DFT calculationsX-ray crystallographyphosphinic acidphospholenephosphorus heterocycles

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Area of Science:

  • Organophosphorus chemistry
  • Heterocyclic chemistry

Background:

  • Phosphabenzenes (phosphinines) are aromatic phosphorus-containing heterocycles.
  • Amino-functionalized phosphabenzenes are of interest due to their unique electronic properties and potential reactivity.
  • Understanding the reactivity of the amino group in phosphabenzenes is crucial for synthetic applications.

Purpose of the Study:

  • To synthesize and characterize a 3-amino-functionalized phosphabenzene.
  • To investigate the basicity and protonation behavior of the amino group.
  • To explore the reactivity of the phosphabenzene-ammonium salt in the presence of water.

Main Methods:

  • Synthesis of 3-amino-functionalized phosphabenzene.
  • Structural characterization using spectroscopic and crystallographic techniques.
  • Protonation studies with HCl.
  • Deuterium labeling experiments.
  • Quantum chemical calculations.

Main Results:

  • Successful synthesis and characterization of 3-(dimethylamino)phosphabenzene.
  • The amino group exhibits weak interaction with the aromatic system, showing basic character and undergoing protonation.
  • The phosphabenzene-ammonium salt undergoes a novel, selective ring contraction to a hydroxylphospholene oxide in aqueous conditions.
  • A reaction mechanism for the ring contraction was proposed and supported by experimental and computational data.

Conclusions:

  • 3-Amino-phosphabenzenes possess unique reactivity distinct from pyridines.
  • The observed ring contraction represents a new transformation for phosphabenzene derivatives.
  • The proposed mechanism provides insight into the reaction pathway of phosphabenzene-ammonium salts in water.