Halomethyl-metal compounds. XIII. Preparation of gem-difluorocyclopropanes by iodide ion-induced CF2 transfer from trimethyl (trifluoromethyl) tin

D Seyferth, H Dertouzos, R Suzuki…

Index: Seyferth,D. et al. Journal of Organic Chemistry, 1967 , vol. 32, p. 2980 - 2984

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Citation Number: 67

Abstract

The action of sodium iodide on trimethyl (trifluoromethy1) tin in DME in the presence of an olefin gives gem-difluorocyclopropanes in yields ranging from moderate to excellent according to the equation Me3SnCF3+ NaI+ olefin+ Me3SnI+ NaF+ gem- difluorocyclopropane. It is suggested that the mechanism of this reaction involves nucleophilic attack by iodide ion on tin to displace the trifluoromethyl anion, which then ...

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