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Related Concept Videos

ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

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Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
4.5K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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

4.6K
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...
4.6K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

5.0K
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...
5.0K
Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

3.2K
When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...
3.2K
Directing Effect of Substituents: meta-Directing Groups01:09

Directing Effect of Substituents: meta-Directing Groups

5.0K
Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the...
5.0K
Directing Effect of Substituents: ortho–para-Directing Groups01:14

Directing Effect of Substituents: ortho–para-Directing Groups

6.4K
Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate...
6.4K

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Plasmid-derived DNA Strand Displacement Gates for Implementing Chemical Reaction Networks
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Direct functionalization with complete and switchable positional control: free phenol as a role model.

Da-Gang Yu1, Francisco de Azambuja, Frank Glorius

  • 1Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149 Münster (Germany) http://www.uni-muenster.de/Chemie.oc/glorius/

Angewandte Chemie (International Ed. in English)
|June 26, 2014
PubMed
Summary
This summary is machine-generated.

Recent advances in transition-metal catalysis enable site-selective functionalization of phenols. These methods offer switchable control for transforming core structures, paving the way for new chemical synthesis strategies.

Keywords:
CH activationCO activationcatalysisfree phenolselectivity

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Phenols are versatile building blocks in organic synthesis.
  • Direct functionalization of phenols remains challenging due to regioselectivity issues.
  • Site-selective transformations are crucial for complex molecule synthesis.

Purpose of the Study:

  • To highlight recent breakthroughs in site-selective phenol functionalization.
  • To showcase transition-metal-catalyzed C-O and C-H bond activation strategies.
  • To demonstrate switchable positional control in phenol transformations.

Main Methods:

  • Review of transition-metal-catalyzed reactions.
  • Analysis of C-O bond activation pathways.
  • Analysis of C-H bond activation pathways.
  • Discussion of regioselectivity control mechanisms.

Main Results:

  • Demonstration of site-selective functionalization of free phenols.
  • Highlighting complete and switchable positional control.
  • Showcasing the utility of C-O and C-H bond activation.
  • Establishing phenols as role models for controlled transformations.

Conclusions:

  • Transition-metal catalysis provides powerful tools for phenol functionalization.
  • Achieved site-selectivity and switchable control offer new synthetic avenues.
  • These methodologies serve as models for controlling transformations of other core structures.