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The Hofmann rearrangement (Hofmann degradation) is the organic reaction of a primary amide to a primary amine with one less carbon atom. [1] [2] [3] The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate.
In this context, the reaction is also known as Saytzeff's isocyanide test. [2] In this reaction, the analyte is heated with alcoholic potassium hydroxide and chloroform. If a primary amine is present, the isocyanide (carbylamine) is formed, as indicated by a foul odour. The carbylamine test does not give a positive reaction with secondary and ...
In the carbylamine reaction (also known as the Hofmann isocyanide synthesis) alkali base reacts with chloroform to produce dichlorocarbene. The carbene then converts primary amines to isocyanides. Illustrative is the synthesis of tert -butyl isocyanide from tert -butylamine in the presence of catalytic amount of the phase transfer catalyst ...
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The reaction center can be a p-or sp n-orbital (Woodward-Hoffmann symbol ω), a conjugated system (π) or even a sigma bond (σ). The relationship is antarafacial when opposite faces of the π system or isolated orbital are involved in the process (think anti). For a σ bond, it corresponds to involvement of one "interior" lobe and one ...
The Ugi reaction has been applied in combination with an intramolecular Diels-Alder reaction [16] in an extended multistep reaction. A reaction in its own right is the Ugi–Smiles reaction with the carboxylic acid component replaced by a phenol. In this reaction the Mumm rearrangement in the final step is replaced by the Smiles rearrangement. [17]
Thermolysis converts 1 to (E,E) geometric isomer 2, but 3 to (E,Z) isomer 4.. The Woodward–Hoffmann rules (or the pericyclic selection rules) [1] are a set of rules devised by Robert Burns Woodward and Roald Hoffmann to rationalize or predict certain aspects of the stereochemistry and activation energy of pericyclic reactions, an important class of reactions in organic chemistry.