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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
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Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Gassman's cationic [2 + 2] cycloadditions using temporary tethers.

Jun Deng1, Richard P Hsung, Changhong Ko

  • 1Division of Pharmaceutical Sciences and Department of Chemistry, Rennebohm Hall, 777 Highland Avenue, University of Wisconsin, Madison, Wisconsin 53705-2222, USA.

Organic Letters
|October 27, 2012
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method for creating cyclobutane structures using temporary tethers. This approach, inspired by Gassman

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Gassman's cationic [2 + 2] cycloaddition is a key reaction in organic synthesis.
  • Temporary tethering strategies are valuable for controlling reactivity and selectivity.

Purpose of the Study:

  • To develop an intermolecular version of Gassman's cationic [2 + 2] cycloaddition.
  • To explore the use of hydrazine and hydroxyamide as temporary tethers in cycloaddition reactions.

Main Methods:

  • Utilizing temporary tethering with hydrazine and hydroxyamide.
  • Performing intermolecular cationic [2 + 2] cycloaddition under acidic conditions.

Main Results:

  • Achieved a novel intermolecular equivalent of Gassman's reaction.
  • Generated unique cyclobutane manifolds with high regio- and stereoselectivity.
  • Demonstrated the robustness of hydrazine and hydroxyamide under acidic cycloaddition conditions.

Conclusions:

  • Hydrazine and hydroxyamide serve as effective temporary tethers in this cycloaddition.
  • The developed method offers a new route to complex cyclobutane structures.
  • This work expands the utility of temporary tethering in synthetic organic chemistry.