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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
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Skeletal Rearrangement of Biaryls via Rhodium-Azirine Intermediate: A Route to Solid-State Emissive Polycyclic

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Researchers developed a rhodium-catalyzed reaction for creating fluorescent spirocyclic cycloheptatrienes from biaryl alkynylsulfamates. This novel cascade process expands nitrene chemistry beyond traditional mechanisms.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Materials Science

Background:

  • Biaryl alkynylsulfamates are versatile precursors.
  • Nitrene-alkyne cyclization is a known reaction.
  • Spirocyclic compounds and fluorescent materials are of significant interest.

Purpose of the Study:

  • To develop a rhodium-catalyzed cascade reaction for synthesizing rigid, spirocyclic cycloheptatrienes.
  • To explore a novel nitrene-mediated rearrangement pathway.
  • To create photoactive scaffolds with strong solid-state fluorescence.

Main Methods:

  • Rhodium-catalyzed cascade reaction of biaryl alkynylsulfamates.
  • Mechanistic studies including density functional theory (DFT) calculations.
  • Analysis of the resulting spirocyclic cycloheptatrienes for fluorescence properties.

Main Results:

  • Successful synthesis of rigid, spirocyclic cycloheptatrienes.
  • Observation of strong solid-state fluorescence in the products.
  • Identification of a rhodium-bound azirine intermediate.
  • Elucidation of a noncarbene-based, dearomative single-carbon insertion pathway.
  • Expansion of nitrene-mediated rearrangement mechanisms beyond Büchner-type reactions.

Conclusions:

  • The developed method provides a modular route to complex, photoactive spirocyclic scaffolds.
  • The cascade process leverages skeletal rigidity for efficient transformation.
  • The findings broaden the understanding of nitrene chemistry and catalytic rearrangements.