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The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Structure-property-reactivity studies on dithiaphospholes.

Darren M C Ould1, Thao T P Tran2, Jeremy M Rawson2

  • 1Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Cardiff, CF10 3AT, Cymru/Wales, UK. melenr@cardiff.ac.uk.

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|November 6, 2019
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Summary
This summary is machine-generated.

New benzo-fused 1,3,2-dithiaphospholes were synthesized from dithiols and phosphorus trihalides. These compounds show diverse reactivity, including phosphenium cation formation and use in reduction catalysis.

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Area of Science:

  • Organophosphorus chemistry
  • Heterocyclic chemistry
  • Synthetic organic chemistry

Background:

  • 1,3,2-Dithiaphospholes are heterocyclic compounds containing phosphorus, sulfur, and carbon.
  • Their synthesis and reactivity are of interest in organophosphorus chemistry.

Purpose of the Study:

  • To synthesize novel benzo-fused 1,3,2-dithiaphospholes.
  • To investigate the chemical reactivity of these new compounds.
  • To evaluate their potential as pre-catalysts in reduction reactions.

Main Methods:

  • Reaction of toluene-3,4-dithiol and benzene dithiol with phosphorus(iii) trihalides.
  • Characterization of the resulting benzo-fused 1,3,2-dithiaphospholes.
  • Investigation of reactions including halogen abstraction, substitution, and reduction.
  • Comparative study of catalytic activity in aldehyde reduction with pinacolborane.

Main Results:

  • Successful synthesis of benzo-fused 1,3,2-dithiaphospholes (RC6H3S2PX).
  • Demonstrated reactivity including formation of phosphenium cations, substitution with LiHMDS, and reduction to P-P bonded dimers.
  • Dithiaphospholes showed distinct reactivity as pre-catalysts in aldehyde reduction compared to related dioxaphospholes and diazaphospholes.

Conclusions:

  • Benzo-fused 1,3,2-dithiaphospholes represent a new class of organophosphorus compounds.
  • These compounds exhibit versatile reactivity profiles.
  • Their catalytic performance in reduction reactions highlights structural influences on reactivity.