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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Ring-Closing Disulfenylation of Alkenoic Thioester
Kanaru Sasaki1, Miari Kurihara1, Hiroki Shigehisa1
1Faculty of Pharmacy, Musashino University, 1-1-20 Shinmachi Nishitokyo, Tokyo 202-8585, Japan.
The Journal of Organic Chemistry
|September 26, 2024
Summary
Alkenoic thioesters are effective nucleophiles in ring-closing disulfenylation reactions. Using hexafluoroisopropanol with electrophilic sulfur reagents enhances product yield and offers advantages over benzyl sulfide.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Ring-closing disulfenylation reactions are important synthetic transformations.
- Traditionally, benzyl sulfide has been used as a nucleophile in these reactions.
Purpose of the Study:
- To demonstrate the efficacy of alkenoic thioesters as nucleophiles in ring-closing disulfenylation.
- To investigate the use of hexafluoroisopropanol and electrophilic sulfur reagents to enhance reaction outcomes.
- To compare the performance of thioesters with benzyl sulfide.
Main Methods:
- Experimental investigation of ring-closing disulfenylation using alkenoic thioesters.
- Utilizing hexafluoroisopropanol as a reaction medium.
- Employing electrophilic sulfur reagents.
- Experimental and theoretical evidence gathering.
- Substrate scope exploration.
Main Results:
- Alkenoic thioesters were successfully employed as nucleophiles in ring-closing disulfenylation.
- Reaction in hexafluoroisopropanol with electrophilic sulfur reagents significantly enhanced product yield.
- Thioesters demonstrated superiority over traditional benzyl sulfide.
- Factors influencing reaction selectivity and yield were identified.
Conclusions:
- Alkenoic thioesters represent a novel and effective class of nucleophiles for ring-closing disulfenylation.
- Hexafluoroisopropanol and specific electrophilic sulfur reagents optimize the reaction.
- This study provides valuable insights into reaction mechanisms and scope for synthetic chemists.
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