Generation of Acyl Radical Equivalents by Cathodic Reduction of Acyl Tributylphosphonium Ions

Article abstract of DOI:10.1246/cl.1995.249

The species generated by one-electron transfer to acyl tributylphosphonium ions has proved to be potent acyl radical equivalents by the results that unsubstituted and 6-phenyl- substituted 5-hexenoic acids were transformed into cyclopentanones by the electrolysis in the presence of Bu3P in an undivided cell, although the yields were not satisfactory due to the formation of 5-hexen-1-als via further one-electron reduction of the radicals before their cyclization.