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Halogens03:01

Halogens

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Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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sp3d and sp3d 2 Hybridization
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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Functionalized Pentafluoroethylphosphanes.

Nadine Allefeld1, Beate Neumann1, Hans-Georg Stammler1

  • 1Fakultät für Chemie, Anorganische Chemie II, Centrum für Molekulare Materialien, Universität Bielefeld, Universitätsstrasse 25, 33615 Bielefeld (Germany).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 17, 2015
PubMed
Summary
This summary is machine-generated.

This study introduces bis(diethylamino)pentafluoroethylphosphane as a key precursor for novel functionalized pentafluoroethylphosphanes. New synthetic routes and reactions were developed, including coordination chemistry and P-C bond formation for creating stereocenters.

Keywords:
fluorinefunctionalizationphosphinic acidphosphorustransition metals

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Area of Science:

  • Organophosphorus Chemistry
  • Fluorine Chemistry
  • Coordination Chemistry

Background:

  • Aminophosphanes, particularly perfluoroalkyl substituted ones, possess unique coordination properties.
  • Pentafluoroethylphosphanes are valuable building blocks in synthetic chemistry.

Purpose of the Study:

  • To explore the synthetic utility of bis(diethylamino)pentafluoroethylphosphane.
  • To synthesize novel functionalized pentafluoroethylphosphanes and investigate their reactivity.
  • To develop new methods for P-C bond formation.

Main Methods:

  • Synthesis of bis(diethylamino)pentafluoroethylphosphane.
  • Reactions with platinum(II) and palladium(II) chlorides.
  • Treatment with hydrogen bromide to form (C2F5)PBr2.
  • Hydrolysis to yield phosphinic acid.
  • Addition reactions of the phosphinic acid to carbonyl compounds.

Main Results:

  • Trans-[Cl2M{P(C2F5)(NEt2)2}2] complexes were synthesized with PtCl2 and PdCl2.
  • The novel compound (C2F5)PBr2 was prepared and converted to C2F5PH2 and C2F5PF2.
  • Acidic hydrolysis yielded the phosphinic acid C2F5P(O)(OH)H, whose anion was structurally characterized.
  • The phosphinic acid underwent P-C bond formation with acetone and salicyl aldehyde.

Conclusions:

  • Bis(diethylamino)pentafluoroethylphosphane is a versatile precursor for diverse pentafluoroethylphosphane derivatives.
  • New synthetic pathways and functionalization strategies were established.
  • The developed methods enable the synthesis of organophosphorus compounds with potential applications in catalysis and stereoselective synthesis.