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Related Concept Videos

Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

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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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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

2.3K
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...
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Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

2.9K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.4K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
8.4K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

10.0K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Continuous-/Micro-Flow Reactions Using Highly Electrophilic PCl3 and POCl3.

Hiroshi Kitamura1, Shinichiro Fuse1

  • 1Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University Furo-cho, Chikusa-ku, Nagoya, 464-8601, Japan.

Chempluschem
|May 24, 2023
PubMed
Summary

Continuous-flow technology offers a safer and more efficient method for synthesizing organophosphorus compounds using reactive phosphorus trichloride (PCl3) and phosphorus oxychloride (POCl3). This approach mitigates risks associated with exothermic reactions and overreactions, improving industrial applications.

Keywords:
Vilsmeier-Haack reactioncontinuous-flowmicro-flowphosphorus trichloridephosphoryl chloride

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Post Column Derivatization Using Reaction Flow High Performance Liquid Chromatography Columns
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Area of Science:

  • Organic Chemistry
  • Chemical Engineering
  • Process Chemistry

Background:

  • Phosphorus trichloride (PCl3) and phosphorus oxychloride (POCl3) are key industrial phosphorus sources.
  • Highly reactive PCl3 and POCl3 often lead to overreactions and exothermic hazards.
  • Milder reagents like phosphoramidites present challenges such as high cost, waste generation, and harsh reaction conditions.

Purpose of the Study:

  • To review recent advancements in utilizing continuous-flow and micro-flow technologies for reactions involving PCl3 and POCl3.
  • To highlight how flow chemistry addresses limitations of traditional batch processes with these reagents.

Main Methods:

  • Application of continuous-flow reactors for phosphorus-containing compound synthesis.
  • Utilizing micro-flow technology for precise control over reaction parameters (time, temperature).
  • Investigating reactions involving phosphorus trichloride (PCl3) and phosphorus oxychloride (POCl3) in flow systems.

Main Results:

  • Flow technology enables precise control, suppressing undesired side reactions.
  • Exothermic reactions involving PCl3 and POCl3 can be safely managed in flow reactors.
  • Continuous and micro-flow systems offer improved selectivity and safety compared to batch methods.

Conclusions:

  • Continuous-flow and micro-flow technologies are promising solutions for overcoming challenges in PCl3 and POCl3 chemistry.
  • These technologies facilitate safer, more controlled, and potentially more efficient synthesis of organophosphorus compounds.
  • The review underscores the potential of flow chemistry in industrial-scale production using reactive phosphorus reagents.