Oxidation and chlorination reactions of perfluoroketene-N,S-acetals |
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Authors: | Sergiy S Mykhaylychenko Jean-Philippe Bouillon |
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Institution: | a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5, Murmanska, 02094 Kiev, Ukraine b Laboratoire Sciences et Méthodes Séparatives (SMS), EA 3233, Université de Rouen, IRCOF, F-76821 Mont-Saint-Aignan Cedex, France |
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Abstract: | The paper presents the results of the investigation of oxidation and chlorination reactions of perfluoroketene-N,S-acetals. Oxidation reactions of perfluoroketene-N,S-acetals proved to be dependent on the nature of oxidizing agent and led to the formation of corresponding sulfone in the case of m-chloroperbenzoic acid or amides of α-H-perfluoroalkane carboxylic acids in the case of tert-butyl hydroperoxide or hydrogen peroxide. Reaction of 1-tert-butylsulfanyl-2,3,3,4,4,4-hexafluoro-1-N-methyl,N-((S)-α-methylbenzyl)amino]-but-1-ene with sulfuryl chloride demonstrated the chlorination of perfluoroketene-N,S-acetals as a new approach in the synthesis of chiral α-chloro perfluoroalkane carboxylic acid amides. |
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Keywords: | Fluorine Sulfur Oxidation Ketene-N S-acetal Perfluoroalkane carboxylic acid derivative Chiral induction |
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