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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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B-substituted group 1 phosphides: synthesis and reactivity.

Michal Aman1, Libor Dostál1, Aleš Růžička1

  • 1Department of General and Inorganic Chemistry, University of Pardubice, 532 10 Pardubice, Czech Republic. roman.jambor@upce.cz.

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|November 2, 2023
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New B-substituted phosphides were synthesized from 1-boryl-8-phosphinonaphthalenes. These compounds readily react with chalcogens and organic substrates, forming novel B-coordinated compounds and demonstrating potential in synthetic chemistry.

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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Synthetic Chemistry

Background:

  • 1-Boryl-8-phosphinonaphthalenes serve as versatile precursors in organophosphorus and organoboron chemistry.
  • The synthesis of novel phosphide compounds with unique coordination environments is crucial for advancing chemical synthesis.
  • Understanding the reactivity of B-substituted phosphides with various substrates expands their synthetic utility.

Purpose of the Study:

  • To synthesize and characterize novel B-substituted phosphides derived from 1-boryl-8-phosphinonaphthalenes.
  • To investigate the reactivity of these phosphides with elemental chalcogens and organic substrates.
  • To explore the formation of new B-coordinated compounds, including diphosphines and phosphatetrylenes.

Main Methods:

  • Preparation of 1-boryl-8-phosphinonaphthalenes (1 and 2).
  • Reduction of precursors using magnesium, sodium, or potassium to yield neutral compounds and group 1 phosphides.
  • Reactions of the synthesized phosphides with chalcogens, carbonyl compounds, and organometallic reagents.
  • Structural characterization of the resulting compounds using spectroscopic and crystallographic techniques.

Main Results:

  • Synthesis of neutral dimers and a rare B ← P coordinated diphosphine.
  • Formation of bulky group 1 phosphides (5 and 6) via reduction with alkali metals.
  • Successful activation of elemental chalcogens (O, S, Se) by phosphide 5, yielding B-substituted chalcogenophosphinites without over-oxidation.
  • Demonstration of phosphide 5's tolerance towards polar C=O bonds, leading to reactions with diketones and acyl chlorides.
  • Preparation of B-coordinated phosphatetrylenes (12 and 13) through substitution reactions of phosphide 5.

Conclusions:

  • Novel B-substituted phosphides were successfully synthesized and characterized.
  • These phosphides exhibit diverse reactivity, enabling the formation of unique B- and P-containing compounds.
  • The study highlights the potential of these compounds as building blocks in synthetic chemistry, particularly for creating B-coordinated species.