ABSTRACT
I. Introduction 247
II. Electrochemical Oxidation and Reduction 248
III. Disp roport ionation 250
IV. Chemical Oxidation 251
A . By Gaining Oxygen 251 B. By Losing Hydrogen 261
V. Chemical Reduction 262
References 268
I. INTRODUCTION
Enamines are unusually susceptible to oxidation, and their immonium salts are readily reduced. The re latively narrow range o f reactions that will be defined as oxidation reactions in this chapter fall into one o f the following three categories: (a ) a reaction in which an electron is completely lost from the enamine; (b ) a reaction in which an oxygen (o r a closely related proxy such as a highly oxidized n itrogen ) either replaces a hydrogen in the enamine or adds to the enamine; and (c ) a reaction in which hydrogens are lost. Reduction reactions will be considered the converse reactions, namely: the complete gain o f an electron by the enamine, replacement o f nitrogen by hydrogen, or addition o f hydrogen to the enamine.
