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Related Concept Videos

Cationic Chain-Growth Polymerization: Mechanism00:57

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,...
Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael acceptor.
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.
Cycloaddition Reactions: Overview01:16

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.
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

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,...
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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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Templating irreversible covalent macrocyclization by using anions.

Evgeny A Kataev1, Grigory V Kolesnikov, Rene Arnold

  • 1Institut für Chemie, Technische Universität Chemnitz, Strasse der Nationen, 62, 09111 Chemnitz, Germany. evgeny.kataev@chemie.tu-chemnitz.de

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 1, 2013
PubMed
Summary

Inorganic anions act as templates to guide the formation of macrocyclic amides. Controlling reaction conditions and understanding intermediate structures are key to maximizing product yields.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Macrocyclic amides are important compounds with diverse applications.
  • Template-directed synthesis offers a pathway to control macrocycle formation.

Purpose of the Study:

  • To investigate the use of inorganic anions as templates in macrocyclic amide synthesis.
  • To elucidate the reaction mechanisms and factors influencing product distribution.

Main Methods:

  • Reaction of diamines with activated diacids under controlled conditions.
  • Utilized various analytical techniques to study reaction kinetics and intermediate structures.

Main Results:

  • Demonstrated a significant template effect using inorganic anions.
  • Identified intermediate structure as crucial for product distribution.
  • Macrocyclization under kinetic control is influenced by template concentration, building block rigidity, and anion affinities.

Conclusions:

  • Inorganic anions effectively template the synthesis of macrocyclic amides.
  • Optimizing reaction parameters like template amount and building block conformation is essential for high yields.