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C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

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The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

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Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

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In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
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Selective C(aryl)-O bond cleavage in biorenewable phenolics.

Gilles De Smet1, Xingfeng Bai1, Bert U W Maes1

  • 1Organic Synthesis Division (ORSY), Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium.

Chemical Society Reviews
|April 18, 2024
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Summary

This study reviews selective reduction reactions for converting lignin-derived phenolics into valuable products. It covers hydrodeoxygenation, hydrodemethoxylation, and hydrodehydroxylation for C-O bond activation in biorefining.

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Area of Science:

  • Chemical Engineering
  • Green Chemistry
  • Biomass Conversion

Background:

  • Biorefining of lignocellulosic biomass yields oxygen-rich phenolics like guaiacols and syringols.
  • These compounds possess challenging C-O bonds, hindering selective functional group removal.
  • Technical lignin processing is difficult, yielding lower monomer quantities.

Purpose of the Study:

  • To provide an overview of selective reduction reactions for C-O bond activation in phenolic compounds.
  • To discuss challenges and methods for hydrodeoxygenation, hydrodemethoxylation, and hydrodehydroxylation.
  • To explore alternative transformations and green chemistry aspects of lignin valorization.

Main Methods:

  • Review of selective hydrodeoxygenation, hydrodemethoxylation, and hydrodehydroxylation techniques.
  • Analysis of reactions using model compounds (guaiacols, syringols) and real lignin mixtures.
  • Discussion of C(aryl)-OH derivatization and subsequent transformations.

Main Results:

  • Complete hydrodeoxygenation yields benzene, alkylated derivatives (BTX), but risks overreduction.
  • Hydrodemethoxylation selectively removes methoxy groups, producing phenols.
  • Hydrodehydroxylation targets hydroxy groups, yielding anisoles, while preserving methoxy groups.

Conclusions:

  • Selective C-O bond activation is crucial for valorizing lignin-derived phenolics.
  • Different reduction strategies offer pathways to specific product classes (BTX, phenols, anisoles).
  • Green chemistry principles are vital for efficient and sustainable lignin biorefining.