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The Phosphorus Cycle01:21

The Phosphorus Cycle

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Unlike carbon, water, and nitrogen, phosphorus is not present in the atmosphere as a gas. Instead, most phosphorus in the ecosystem exists as compounds, such as phosphate ions (PO43-), found in soil, water, sediment and rocks. Phosphorus is often a limiting nutrient (i.e., in short supply). Consequently, phosphorus is added to most agricultural fertilizers, which can cause environmental problems related to runoff in aquatic ecosystems.
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Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Sodium phosphaethynolate as a building block for heterocycles.

Xiaodan Chen1, Simone Alidori, Florian Frank Puschmann

  • 1Department of Chemistry and Applied Biosciences, ETH Zurich, 8093 Zurich (Switzerland).

Angewandte Chemie (International Ed. in English)
|January 24, 2014
PubMed
Summary

Researchers developed a new method to synthesize functionalized phosphorus heterocycles using the phosphaethynolate anion. This approach enables the creation of novel building blocks for coordination chemistry and material science applications.

Keywords:
cycloadditionmultiple bondsphosphininesphosphorus heterocyclessodium phosphaethynolate

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Area of Science:

  • Synthetic inorganic chemistry
  • Organophosphorus chemistry
  • Materials science

Background:

  • Phosphorus heterocycles are increasingly important functional components.
  • Challenges exist in the straightforward, large-scale synthesis of functionalized heterocycles.

Purpose of the Study:

  • To report a novel synthetic route to sterically unprotected and functionalized hydroxy-substituted phosphorus heterocycles.
  • To utilize the phosphaethynolate anion as a versatile building block.

Main Methods:

  • Employing the phosphaethynolate (OCP)(-) anion as a key synthon.
  • Facile functionalization of the resulting anionic heterocycles.

Main Results:

  • Successful synthesis of various functionalized hydroxy-substituted phosphorus heterocycles.
  • The synthesized heterocycles are themselves anions, allowing further modification.

Conclusions:

  • The phosphaethynolate anion is a valuable building block for novel phosphorus heterocycles.
  • These new heterocycles offer potential applications in coordination chemistry and material science.