Ultrasonic Effects on Electroorganic Processes. Part 9. Current Efficiency and Product Selectivity in the Electroreduction of Alkyl Halides to Alkyl Stannanes at a Reactive Tin Cathode

Article abstract of DOI:10.1246/bcsj.71.397

The ultrasonic effects on the electroreduction of methyl and allyl halides (RX) to the corresponding stannanes (R₃SnSnR₃ and R₄Sn) at a reactive (consumable) tin cathode were examined. The current efficiency and product selectivity for the reduction were found to be greatly affected by ultrasonic irradiation. For instance, the selectivity for (CH₃)₃SnSn(CH₃)₃ to (CH₃)₄Sn from CH₃I was significantly increased under irradiation. This fact is rationalized as being due to because the intermediate species [(CH₃)₃Sn·] formed by the primary one-electron reduction of CH₃I are activated for their coupling by mobilization on/from the cathode surface under irradiation. On the other hand, the ultrasonic effects on the reduction of CH₃Br and C₃H₅Br seemed to be slightly different from those in the reduction of CH₃I.