Tetrahedron

Nucleophilic chain substitution on perfluoroketene dithioacetals by ethyl 2-trimethysilyl acetate. Application to the synthesis of 2-trifluoromethyl succinic acid …

C Brulé, JP Bouillon, C Portella

Index: Brule, Cedric; Bouillon, Jean-Philippe; Portella, Charles Tetrahedron, 2004 , vol. 60, # 44 p. 9849 - 9855

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Citation Number: 15

Abstract

A highly efficient substitution of the vinyl fluoride of perfluoroketene dithioacetals was achieved using trimethylsilylacetate to give 2-perfluoroalkyl succinic acid derivatives and 2- trifluoromethyl succinimides. This chain process was initiated by a catalytic amount of fluoride salt, whereas reaction failed with the corresponding lithium enolate.