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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.4K
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.
2.4K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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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.
29.8K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

8.2K
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.
8.2K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

2.3K
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...
2.3K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.4K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.4K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.2K
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.
2.2K

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Intramolecular donor-acceptor cyclopropane ring-opening cyclizations.

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Donor-acceptor cyclopropanes undergo intramolecular reactions for creating complex molecular structures. This review highlights their cycloisomerizations, cycloadditions, and rearrangements, showcasing their utility in synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Donor-acceptor (D-A) cyclopropanes are valuable synthons in organic chemistry.
  • Their intermolecular reactivity is well-documented, but intramolecular transformations are less explored.

Purpose of the Study:

  • To review recent intramolecular reactions of D-A cyclopropanes (2009-2013).
  • To highlight their application in constructing carbocyclic and heterocyclic scaffolds.
  • To underscore their role in natural product synthesis.

Main Methods:

  • Focus on intramolecular cycloisomerizations.
  • Exploration of formal cycloadditions and umpolung reactions.
  • Review of rearrangements and ring-opening lactonizations/lactamizations.

Main Results:

  • D-A cyclopropanes enable diverse intramolecular cyclization pathways.
  • These reactions facilitate the synthesis of complex molecular architectures.
  • Demonstrated utility in the total synthesis of natural products.

Conclusions:

  • Intramolecular reactions of D-A cyclopropanes offer efficient routes to diverse scaffolds.
  • This chemistry provides powerful tools for synthetic organic chemists.
  • Further exploration of D-A cyclopropane intramolecular reactivity is warranted.