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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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Radicals01:27

Radicals

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Roots, often written as radicals, identify the quantity that must be raised to a specific exponent to produce a given value. A radical expression consists of two main components: the radicand, which is the value placed inside the root symbol, and the index, which indicates the degree of the root being taken. The notation n√a indicates the principal nth root of a. If n equals 2, the operation is the square root, while n = 3 defines the cube root. When n is even, a negative radicand does...
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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Radical Equations01:26

Radical Equations

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Radical equations are mathematical expressions in which the variable is found within a radical, most commonly a square root or cube root. These equations frequently arise in science, engineering, and real-world measurements involving nonlinear relationships. To solve a radical equation, the standard procedure is to isolate the radical expression and then eliminate the radical by raising each side to a power equal to the index of the radical. This process may lead to extraneous...
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Radical Formation: Overview01:03

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A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
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Stable Boron Dithiolene Radicals.

Yuzhong Wang1, Yaoming Xie1, Pingrong Wei1

  • 1Department of Chemistry and the Center for Computational Chemistry, The University of Georgia, Athens, GA, 30602-2556, USA.

Angewandte Chemie (International Ed. in English)
|May 15, 2018
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel boron dithiolene radicals through low-temperature reactions. These radicals exhibit unique B-C bond activation, leading to a dithiocarbamate zwitterion, offering insights into radical chemistry and organoboron compounds.

Keywords:
B−C activationboroncarbenesdithiolenesradicals

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Area of Science:

  • Organometallic Chemistry
  • Radical Chemistry
  • Boron Chemistry

Background:

  • Dithiolene ligands are versatile in coordinating with main group elements.
  • Boron halides are common reagents for synthesizing organoboron compounds.
  • Radical species offer unique reactivity pathways in chemical synthesis.

Purpose of the Study:

  • To synthesize and characterize novel dibromoboron and dicyclohexylboron dithiolene radicals.
  • To investigate the reactivity and structural properties of these boron dithiolene radicals.
  • To explore the potential for B-C bond activation in these radical systems.

Main Methods:

  • Low-temperature reactions of lithium dithiolene radical with boron bromide and dicyclohexylboron chloride.
  • Single-crystal X-ray diffraction for structural elucidation.
  • UV/Vis and Electron Paramagnetic Resonance (EPR) spectroscopy for characterization.
  • Computational studies to probe radical nature.

Main Results:

  • Successful synthesis of dibromoboron dithiolene radical (2•) and dicyclohexylboron dithiolene radical (3•).
  • Characterization of radicals 2• and 3• using X-ray diffraction, UV/Vis, and EPR spectroscopy.
  • Observation of unexpected thiourea-mediated B-C bond activation in radical 3•, yielding zwitterion 4.
  • Zwitterion 4 identified as a dithiolene-modified carbene complex of a sulfenyl cation.

Conclusions:

  • The study demonstrates the successful synthesis and characterization of novel boron dithiolene radicals.
  • Radical 3• exhibits unique reactivity, undergoing B-C bond activation under mild conditions.
  • The formation of zwitterion 4 provides new insights into the chemistry of dithiolene-metal complexes and carbene species.