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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 bromine molecule...
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Efficient medium ring size bromolactonization using a sulfur-based zwitterionic organocatalyst.

Yi An Cheng1, Tao Chen, Chong Kiat Tan

  • 1Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.

Journal of the American Chemical Society
|September 25, 2012
PubMed
Summary
This summary is machine-generated.

A novel zwitterionic catalyst efficiently synthesizes medium-sized lactones from olefinic acids via catalytic bromolactonization. The reaction performs best at 0 °C, highlighting the catalyst

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Efficient synthesis of medium-sized lactones is crucial for various chemical applications.
  • Traditional methods for lactone synthesis often involve harsh conditions or multiple steps.
  • Development of novel catalytic systems for selective transformations is an active research area.

Purpose of the Study:

  • To report an efficient catalytic bromolactonization method for synthesizing medium-sized lactones.
  • To investigate the use of a zwitterionic catalyst in this transformation.
  • To explore the effect of reaction temperature on the efficiency of the bromolactonization.

Main Methods:

  • Utilized a zwitterionic catalyst for the catalytic bromolactonization of long-chain olefinic acids.
  • Employed N-bromosuccinimide as the stoichiometric halogen source.
  • Conducted reactions at different temperatures (0 °C and room temperature) to assess efficiency.

Main Results:

  • Achieved efficient synthesis of medium-sized lactones from long-chain olefinic acids.
  • The zwitterionic catalyst demonstrated high efficacy in promoting the bromolactonization reaction.
  • Reaction efficiency was significantly higher at 0 °C compared to room temperature.

Conclusions:

  • A novel and efficient catalytic system for bromolactonization has been developed.
  • The zwitterionic catalyst is effective for synthesizing medium-sized lactones.
  • The temperature dependence of the zwitterionic catalyst influences reaction efficiency, favoring lower temperatures.