Diazoketon

Diazoketone is a class of organic compounds characterized by the presence of both a ketone functional group (C=O) and a diazo group (N=N) within the same molecule. The general formula for diazoketones is R-CO-CHN2, where R represents an alkyl or aryl group. These compounds are typically colored, often yellow or orange, due to the extended conjugation involving the diazo group.

Diazoketones are known for their reactivity. The diazo group is a good leaving group, and the adjacent carbonyl group activates the molecule for various chemical transformations. A prominent reaction of diazoketones is their decomposition upon heating or treatment with catalysts, which generates a highly reactive carbene intermediate. This carbene can then undergo a range of reactions, including insertion into C-H bonds, cyclopropanation of alkenes, and Wolff rearrangement. The Wolff rearrangement, in particular, transforms diazoketones into ketenes, which are versatile intermediates in organic synthesis.

Due to their synthetic utility, diazoketones are employed in the synthesis of various organic molecules, including esters, amides, and cyclic compounds. They are also used in the preparation of more complex structures through their participation in cycloaddition reactions. Safety precautions are important when handling diazoketones, as some can be shock-sensitive or potentially explosive, especially in their pure or concentrated forms.