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Introduction
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Reversible Bergman cyclization by atomic manipulation.

Bruno Schuler1, Shadi Fatayer1, Fabian Mohn1

  • 1IBM Research - Zurich, 8803 Rüschlikon, Switzerland.

Nature Chemistry
|February 20, 2016
PubMed
Summary
This summary is machine-generated.

Chemists achieve the first reversible Bergman cyclization, transforming aromatic diradicals into strained diynes on a surface. This breakthrough enables on-demand switching between reactive intermediates for advanced radical chemistry.

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Area of Science:

  • Organic Chemistry
  • Surface Science
  • Supramolecular Chemistry

Background:

  • The Bergman cyclization is a key organic reaction with significant applications.
  • Controlling reactive intermediates like diradicals is crucial for synthetic chemistry.

Purpose of the Study:

  • To demonstrate the first reversible Bergman cyclization on a surface.
  • To explore the distinct properties and on-demand switching of diradical and diyne intermediates.

Main Methods:

  • Utilizing atomic manipulation to induce and control the Bergman cyclization on an ultrathin NaCl film.
  • Employing non-contact atomic force microscopy for atomic-resolution characterization of intermediates.

Main Results:

  • Successfully achieved a reversible Bergman cyclization, converting aromatic diradicals to strained ten-membered diynes and vice versa.
  • Demonstrated on-demand switching between diradical and diyne states via selective C-C bond formation/cleavage.
  • Observed distinct electronic, magnetic, and optical properties for the diradical and diyne.

Conclusions:

  • This work establishes a new paradigm for on-surface radical chemistry using reversible Bergman cyclization.
  • The ability to switch between reactive intermediates opens avenues for novel molecular devices and reactions.