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Reactivity of Enols01:18

Reactivity of Enols

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Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...
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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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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

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

6.6K
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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Carboxylic acid derivatives such as acid halides, anhydrides, esters, and amides undergo nucleophilic acyl substitution reactions with varying degrees of reactivity.
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3.1K
Reactivity of Enolate Ions01:23

Reactivity of Enolate Ions

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Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
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An Isolable Three-Coordinate Germanone and Its Reactivity.

Xuan-Xuan Zhao1, Tibor Szilvási2, Franziska Hanusch1

  • 1Department of Chemistry, WACKER-Institute of Silicon Chemistry and Catalysis Research Center, Technische Universität München, Lichtenbergstraße 4, 85748, Garching bei, München, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 16, 2021
PubMed
Summary

A novel three-coordinate germanone, [IPrN]2 Ge=O, was synthesized and found to be thermally stable. This germanium compound exhibits reactivity with small molecules, mimicking nucleophilic transition-metal oxides.

Keywords:
N-heterocyclic iminesO-atom transfercarbonylsgermanonesmall molecule activation

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Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Main Group Chemistry

Background:

  • Three-coordinate germanium compounds are rare.
  • Germanones, germanium analogues of ketones, are of significant interest due to their unique bonding and reactivity.
  • Understanding the stability and reactivity of low-coordinate germanium species is crucial for advancing main group chemistry.

Purpose of the Study:

  • To synthesize and characterize a novel three-coordinate germanone.
  • To investigate the thermal stability and reactivity of the synthesized germanone.
  • To explore its potential as a mimic of nucleophilic transition-metal oxides.

Main Methods:

  • Isolation and characterization of the three-coordinate germanone, [IPrN]2 Ge=O.
  • Thermal stability studies in arene solvents up to 80°C.
  • Reactivity studies with small molecules, including phenylacetylene and isocyanides.
  • Density Functional Theory (DFT) calculations to investigate reaction mechanisms.

Main Results:

  • Successful isolation of a rare three-coordinate germanone, [IPrN]2 Ge=O.
  • The germanone exhibits high thermal stability in arene solvents.
  • The terminal Ge=O bond is highly polarized, enabling reactivity with small molecules.
  • The compound mimics nucleophilic transition-metal oxides through reactions like O-atom transfer.
  • DFT calculations reveal a [2+2] cycloaddition mechanism for the O-atom transfer reaction.

Conclusions:

  • The synthesized three-coordinate germanone is a stable yet reactive species.
  • Its reactivity profile, particularly O-atom transfer, positions it as a functional mimic of transition-metal oxides.
  • The study provides insights into the chemistry of low-coordinate germanium compounds and their potential applications.