The Reactions of Aliphatic Diazocompounds with Acids

Abstract

This chapter illustrates the reactions of aliphatic diazocompounds with acids. The mechanism of these reactions probably embrace that of the most common method of diazoalkylation used in organic synthesis, while the formation of diazonium ion intermediates makes it an important source of the deamination of aliphatic amines and of other reactions proceeding by way of diazonium ions. The reaction of diphenyldiazomethane, because its kinetics can be followed spectrophotometrically with ease and accuracy, has been widely used in the study of structure reactivity relations of organic acids. Because the simplest diazoalkanes are rather reactive substances, easily decomposed, and handled only with difficulty under quantitative conditions, kinetic investigations have been confined mainly to more stable derivatives, such as diazoesters, diazoketones, and diazosulphones. Two such substrates that have been extensively studied are diazoacetic ester (ethyl diazoacetate) and diphenyldiazomethane. Most diazoalkanes undergo a ready thermal decomposition. The chapter also distinguishes thermal and acid-catalyzed reactions and the thermal reaction is described in the case of diphenyldiazomethane.