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An unexpected synthesis of ketene monothioacetals
Stéphanie Fabre1, Xavier Vila, Samir Z Zard
1Laboratoire de Synthèse Organique associé au C. N. R. S., Département de Chimie, Ecole Polytechnique, F-91128 Palaiseau, France.
Certain dithiocarbonates, also known as xanthates, can transform into ketene monothioacetals. This conversion is achieved by extruding sulfur using a base and an alkylating agent.
Area of Science:
- Organic Chemistry
- Sulfur Chemistry
Background:
- Dithiocarbonates, specifically xanthates, are versatile sulfur-containing organic compounds.
- Understanding the reactivity of dithiocarbonates is crucial for synthetic organic chemistry.
Purpose of the Study:
- To investigate the conversion of dithiocarbonates into ketene monothioacetals.
- To explore the reaction mechanism involving sulfur extrusion.
Main Methods:
- Treatment of dithiocarbonates with a base.
- Alkylation of the intermediate species.
- Analysis of the resulting ketene monothioacetals.
Main Results:
- Successful conversion of dithiocarbonates to ketene monothioacetals was demonstrated.
- The reaction proceeds via sulfur extrusion.
- The methodology offers a new route to ketene monothioacetals.
Conclusions:
- Dithiocarbonates can be readily converted to ketene monothioacetals.
- This reaction provides a valuable synthetic pathway for accessing ketene monothioacetals.
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