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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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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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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Thermal Electrocyclic Reactions: Stereochemistry01:17

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

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4.1K
Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
7.9K
Regioselectivity and Stereochemistry of Hydroboration02:36

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control.

Takuhei Yamamoto1, Jixun Dai1, Neil E Jacobsen1

  • 1Department of Chemistry and Biochemistry, The University of Arizona , Tucson, Arizona 85721, United States.

Organic Letters
|July 13, 2016
PubMed
Summary

Neighboring amide groups enhance thioether electrochemical oxidation. This study reveals amide π orbitals stabilize the resulting sulfur radical cation through two-electron participation, confirmed by NMR spectroscopy.

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Area of Science:

  • Electrochemistry
  • Organic Chemistry
  • Spectroscopy

Background:

  • Thioethers are important organic compounds.
  • Electrochemical oxidation is a key transformation in organic synthesis.
  • Neighboring group participation can influence reaction mechanisms.

Purpose of the Study:

  • To investigate the role of neighboring amide groups in the electrochemical oxidation of thioethers.
  • To elucidate the mechanism of facilitation by amide participation.
  • To characterize the intermediate species formed during the reaction.

Main Methods:

  • Electrochemical oxidation of thioethers.
  • (1)H Nuclear Magnetic Resonance (NMR) spectroscopy in acetonitrile solution.
  • Analysis of conformationally constrained thioether-amide compounds.

Main Results:

  • Electrochemical oxidation of thioethers is significantly facilitated by neighboring amide groups.
  • Spectroscopic analysis confirmed two-electron participation from the amide π2 orbital.
  • This participation stabilizes the intermediate sulfur radical cation.

Conclusions:

  • Neighboring amide participation is a key factor in enhancing thioether electrochemical oxidation.
  • The amide π orbital plays a crucial role in stabilizing the sulfur radical cation intermediate.
  • This finding provides insights into the mechanism of electrochemical oxidation reactions involving thioethers.