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The Chemical Science
Carbylamine reaction
Carbylamine reaction mechanism includes the addition of amine to the intermediate created from the dehydrohalogenation of chloroform. This intermediate is called dichlorocarbene. The carbylamine reaction is also known as Hofmann isocyanide synthesis. It is the reaction of a primary amine, chloroform and a base to synthesize isocyanides. The dichlorocarbene intermediate is very important for this conversion. The carbylamine reaction cannot be used to synthesize isocyanides from secondary or tertiary amines. In general, the carbylamine reaction can be written as –
Mechanism of Carbylamine Reaction:
Dehydrogenation is removal of hydrogen halide from specific substrate of chloroform is the first step, which yields Dichlorocarbene as an intermediate. Dichlorocarbene is a highly reactive intermediate.
The electrophilic dichlorocarbene targets the main amine’s nucleophilic nitrogen.
The hydrochloric acid is then eliminated, resulting in the creation of isonitrile.
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