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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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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Acid-Catalyzed Ring-Opening of Epoxides02:24

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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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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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Programmable divergent electrochemical ring-opening multifunctionalization of strained rings.

Yajuan Li1, Yatao Lang2, Shu-Fan He1

  • 1Frontiers Science Center for Transformative Molecules, State Key Laboratory of Synergistic Chem-Bio Synthesis, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai, People's Republic of China.

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This study introduces a novel electro-oxidation method for functionalizing strained rings, enabling precise control over multiple C-H and C-C bonds. The technique generates diverse oxygenated scaffolds and bicyclic frameworks efficiently.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Methodology

Background:

  • Ring-opening functionalization of strained rings is valuable but challenging.
  • Existing methods struggle with selective control over multiple inert C-H/C-C bonds.
  • Site, regio, and oxidation state control remain unmet challenges.

Purpose of the Study:

  • To develop a multisite programmable, divergent ring-opening functionalization strategy.
  • To overcome limitations in selective C-H/C-C bond functionalization.
  • To enable facile synthesis of diverse multi-oxygenated scaffolds.

Main Methods:

  • Electro-oxidation of continuous C-C bonds and multiple C(sp3)-H bonds.
  • Controlled generation of olefins via an 'olefin slow-release pool' to ensure selectivity.
  • Utilizing direct current electrolysis, rapid alternating polarity electrolysis, and electrophotocatalysis.

Main Results:

  • Achieved precise trioxygenation, tetraoxygenation, and trihalohydroxylation.
  • Demonstrated controllable remote alkenylation.
  • Successfully transformed strained rings into diverse scaffolds like oxazolines, polyols, and polyhalogenated alcohols.

Conclusions:

  • The developed method offers a versatile approach for strained ring functionalization.
  • Enables the synthesis of complex multi-oxygenated structures and bicyclic frameworks.
  • Provides a powerful tool for skeletal editing and accessing novel chemical architectures.