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A novel recyclable sulfur monoxide transfer reagent
R S Grainger1, A Procopio, J W Steed
1Department of Chemistry, King's College London, Strand, London WC2R 2LS, UK. richard.grainger@kcl.ac.uk
Organic Letters
|October 27, 2001
Summary
Researchers synthesized trisulfide 2-oxide and used it to transfer sulfur monoxide to dienes, forming cyclic sulfoxides. These sulfoxides can then be converted into thiophenes via a Pummerer reaction.
Area of Science:
- Organic Chemistry
- Sulfur Chemistry
- Heterocyclic Chemistry
Background:
- Sulfur-containing compounds are crucial in organic synthesis.
- Developing novel methods for sulfur monoxide transfer is of significant interest.
- Thiophenes are important heterocyclic compounds with diverse applications.
Purpose of the Study:
- To prepare and characterize trisulfide 2-oxide.
- To investigate the sulfur monoxide transfer capabilities of trisulfide 2-oxide.
- To explore the synthesis of cyclic sulfoxides and their subsequent conversion to thiophenes.
Main Methods:
- Reduction of disulfide to dithiol followed by trapping with thionyl chloride to form trisulfide 2-oxide.
- Reaction of trisulfide 2-oxide with dienes under thermal conditions.
- Application of the Pummerer reaction to convert cyclic sulfoxides to thiophenes.
Main Results:
- Trisulfide 2-oxide was successfully synthesized.
- Efficient transfer of sulfur monoxide to various dienes was achieved, yielding cyclic unsaturated sulfoxides.
- Good to excellent yields were obtained for the cyclic sulfoxides, with recovery of the starting disulfide.
- Cyclic sulfoxides were effectively transformed into thiophenes using the Pummerer reaction.
Conclusions:
- Trisulfide 2-oxide is a viable reagent for sulfur monoxide transfer.
- This method provides a new route to cyclic sulfoxides and subsequently thiophenes.
- The Pummerer reaction offers a pathway for further functionalization of the thiophene products.