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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.9K
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.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.7K
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.
3.7K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.4K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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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.
2.2K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

5.9K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

4.8K
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Predicting reactivity for bioorthogonal cycloadditions involving nitrones.

Masaya Nakajima1, Didier A Bilodeau2, John Paul Pezacki2

  • 1Graduate School of Pharmaceutical Sciences, Chiba University 1-8-1 Inohana Chuo-ku Chiba 260-8675 Japan m.nakajima@chiba-u.jp.

RSC Advances
|May 6, 2022
PubMed
Summary
This summary is machine-generated.

Nitrones are versatile dipoles used in chemical synthesis and bioorthogonal reactions. Density functional theory and the distortion/interaction model accurately predict nitrone cycloaddition reactivity, enhancing molecular design.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Chemical Biology

Background:

  • Nitrones serve as valuable dipoles in synthetic chemistry and bioorthogonal reactions.
  • Their small size, ease of incorporation into biomolecules, and tunable reactivity make them ideal for biological applications.

Purpose of the Study:

  • To investigate the reactivity of common nitrone cycloadditions using computational methods.
  • To assess the predictive power of Density Functional Theory (DFT) and the distortion/interaction (D/I) model for nitrone cycloadditions.

Main Methods:

  • Utilized Density Functional Theory (DFT) calculations.
  • Applied the distortion/interaction (D/I) model to analyze reaction pathways.

Main Results:

  • DFT and D/I model successfully predicted the relative reactivities of nitrone cycloadditions.
  • Gained insights into factors influencing reactivity for both nitrones and dipolarophiles.

Conclusions:

  • The distortion/interaction (D/I) model is a reliable tool for understanding and predicting nitrone cycloaddition reactivity.
  • Computational approaches enhance the design and application of nitrones in synthesis and bioorthogonal chemistry.