Electrogenerated Superoxide-Initiated Autoxidation. A Convenient Electrochemical Method for the Conversion of Secondary Nitroalkanes to Ketones and the Use of Primary Nitroalkanes as Acyl Anion Equivalents in Michael Reactions

Article abstract of DOI:10.1021/jo00154a009

Electrochemically generated superoxide ion was used as a base to deprotonate secondary nitroalkanes whose anions were then oxidized with molecular oxygen, thereby providing a means of converting the secondary nitro group to a ketone.In addition, the radical anion of azobenzene was used as an electrogenerated base to catalyze the Michael condensation of primary nitroalkanes with a variety of acceptors; subsequent exposure of the Michael adduct to the electrogenerated superoxide-initiated autoxidation provides a one-pot sequence for the β-addition of an acyl anion equivalent.