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Related Concept Videos

Fast Reactions01:27

Fast Reactions

Fast reactions occurring in times shorter than the time needed to mix reactants pose a unique challenge for investigation. In a liquid-phase continuous-flow system, reactants A and B are swiftly pushed into the mixing chamber, where mixing occurs within 1 ms. The reaction mixture then flows through an observation tube, and one measures light absorption to determine species concentrations at various points of the tube. This method is most appropriate when relatively large volumes of reactants...
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only in the...
E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
Reaction Mechanisms: The Steady-State Approximation01:26

Reaction Mechanisms: The Steady-State Approximation

The steady-state approximation, also referred to as the quasi-steady-state approximation to differentiate it from a true steady state, is a widely used method for simplifying calculations in complex reaction mechanisms. This approach is particularly useful when dealing with multi-step reactions that involve reverse reactions or several steps, which can significantly increase mathematical complexity and make the reactions nearly unsolvable analytically.The steady-state approximation operates on...
Coupled Reactions01:17

Coupled Reactions

Cellular processes such as building and breaking down complex molecules occur through stepwise chemical reactions. Some of these chemical reactions are spontaneous and release energy, whereas others require energy to proceed. Cells often couple the energy-releasing reaction with the energy-requiring one to carry out important cell functions. 
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Reaction Mechanisms: Rate-limiting Step Approximation01:29

Reaction Mechanisms: Rate-limiting Step Approximation

The rate-determining step, or RDS, in a chemical reaction is the slowest step that determines the overall reaction rate. It is identified by using the observed rate law and typically involves approximation methods like the RDS approximation or the steady-state approximation.In the RDS approximation, also known as the rate-limiting-step or equilibrium approximation, the reaction mechanism consists of one or more reversible reactions near equilibrium, followed by a slower RDS, and then one or...

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A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor
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The Eschenmoser coupling reaction under continuous-flow conditions.

Sukhdeep Singh1, J Michael Köhler, Andreas Schober

  • 1Institute for Chemistry and Biotechnology, Technische Universität Ilmenau, Weimarerstr. 32, D-98693-Ilmenau.

Beilstein Journal of Organic Chemistry
|September 15, 2011
PubMed
Summary

The Eschenmoser coupling, a key carbon-carbon bond formation, is now efficient for challenging thioamides using flow chemistry. This method achieves high yields rapidly under optimized temperature and pressure conditions.

Keywords:
S-alkylationactivation energyepisulfideflow chemistryketo iminekineticssulfide contractiontriisopropyl phosphite

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • The Eschenmoser coupling is a vital carbon-carbon bond-forming reaction.
  • S-alkylated ternary thioamides/thiolactams facilitate the reaction smoothly.
  • S-alkylated secondary thioamides/thiolactams require harsh conditions (long times, high temperatures) for acceptable yields.

Purpose of the Study:

  • To enhance the Eschenmoser coupling for difficult precursors using flow chemistry.
  • To improve efficiency and reduce reaction times for secondary thioamides/thiolactams.

Main Methods:

  • Utilized a flow chemistry system for enhanced reaction conditions.
  • Investigated reaction kinetics under pressurized conditions (approx. 220 °C).

Main Results:

  • Achieved efficient Eschenmoser coupling of demanding S-alkylated secondary thioamides/thiolactams.
  • Obtained desired products within a 70-second residence time.
  • Demonstrated the method with 15 diverse building block combinations.

Conclusions:

  • Flow chemistry enables efficient Eschenmoser coupling under optimized, high-temperature, pressurized conditions.
  • This approach significantly improves the conversion of challenging thioamide precursors.
  • The study provides a rapid and versatile method for carbon-carbon bond formation.