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Free radical and isomerisation processes during the electrochemical fluorination of n-butyryl chloride, i-butyryl chloride and pivaloyl chloride in anhydrous hydrogen fluoride
Authors:D. Velayutham  K. Kulangiappar  Y. Ram Babu  S. Narayana Reddy  M. Noel
Affiliation:a Central Electrochemical Research Institute, Karaikudi 630006, Tamil Nadu, India
b Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500007, Andhra Pradesh, India
c Central Leather Research Institute, Adyar, Chennai 600020, Tamil Nadu, India
Abstract:Electrochemical perfluorination (ECPF) of the title compounds containing primary, secondary and tertiary carbon atoms was carried out in anhydrous hydrofluoric acid (AHF). Detailed analysis of major and minor products suggest that carbon chain isomerisation involving cyclo-propane intermediate is more prevalent during ECPF of i-butyryl chloride when compared to n-butyryl chloride. Simple statistical probability involving free radical intermediates also support this observation. ECPF involving cyclo-propane intermediate is even more prevalent in pivaloyl chloride containing three methyl substituents. In this case, perfluorinated cyclo-propane intermediates were also observed in the product sample. Distribution of minor perfluorinated and partially fluorinated products also suggest the predominant role of normal free radical pathway involving single-electron transfer.
Keywords:Electrochemical fluorination   n-Butyryl chloride   i-Butyryl chloride   Pivaloyl chloride   cyclo-Propane intermediate
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