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Related Concept Videos

Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

6.9K
Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
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Halogens03:01

Halogens

17.2K
Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

2.6K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
2.6K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
9.3K
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

7.7K
In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
7.7K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

3.0K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
3.0K

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The Portable Chemical Sterilizer PCS, D-FENS, and D-FEND ALL: Novel Chlorine Dioxide Decontamination Technologies for the Military
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Palau'chlor: a practical and reactive chlorinating reagent.

Rodrigo A Rodriguez1, Chung-Mao Pan, Yuki Yabe

  • 1Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society
|April 25, 2014
PubMed
Summary
This summary is machine-generated.

A novel guanidine-based chlorinating reagent, CBMG ("Palau

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Chlorinated arenes and (hetero)arenes are valuable in tuning electronic properties and enabling diversification through cross-coupling reactions.
  • Existing chlorination methods may lack efficiency, safety, or broad substrate scope.

Purpose of the Study:

  • To develop a new, efficient, and safe chlorinating reagent for organic synthesis.
  • To introduce CBMG ("Palau'chlor"), a guanidine-based reagent for chlorination.

Main Methods:

  • Development of a novel guanidine-based chlorinating reagent, CBMG.
  • Testing the reagent's compatibility with various substrates including nitrogen-containing heterocycles, arenes, conjugated π-systems, sulfonamides, and silyl enol ethers.
  • Comparative analysis against existing chlorinating reagents.

Main Results:

  • CBMG ("Palau'chlor") was successfully synthesized and demonstrated as an effective chlorinating agent.
  • The reagent exhibits mild, direct, operationally simple, and safe chlorination.
  • Broad substrate compatibility was observed across diverse organic molecules.
  • CBMG outperformed other known chlorinating reagents in comparative studies.

Conclusions:

  • CBMG ("Palau'chlor") represents a significant advancement in chlorination methodology.
  • This new reagent offers a superior alternative for introducing chlorine atoms into organic molecules.
  • Its versatility and safety profile make it a valuable tool for synthetic chemists.