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Hofmann elimination is an elimination reaction of an amine to form alkenes. The least stable alkene (the one with the fewest substituents on the carbons of the double bond), called the Hofmann product , is formed.
In the Hofmann elimination, treatment of a quaternary ammonium iodide salt with silver oxide produces hydroxide ions, which act as a base and eliminate the tertiary amine to give an alkene. [11] In the Hofmann elimination, the least substituted alkene is typically favored due to intramolecular steric interactions.
In organic chemistry, the E i mechanism (Elimination Internal/Intramolecular), also known as a thermal syn elimination or a pericyclic syn elimination, is a special type of elimination reaction in which two vicinal (adjacent) substituents on an alkane framework leave simultaneously via a cyclic transition state to form an alkene in a syn elimination. [1]
The reverse or retro-Cope elimination has been reported, in which an N,N-disubstituted hydroxylamine reacts with an alkene to form a tertiary N-oxide. [9] [10] The reaction is a form of hydroamination and can be extended to the use of unsubstituted hydroxylamine, in which case oximes are produced. [11]
Elimination reaction of cyclohexanol to cyclohexene with sulfuric acid and heat [1] An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. [2] The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction ...
The Mannich base is then subjected to methylation or N-oxidation to give a trimethylammonium salt or amine N-oxide, which is then subjected to Hofmann elimination or Cope elimination, respectively to give the α-methylene carbonyl compound. If the Hofmann elimination is used, the process can be represented as follows:
The final elimination of oxaphosphetanes 4a and 4b yield (E)-alkene 5 and (Z)-alkene 6, with the by-product being a dialkyl-phosphate. The mechanism of the Horner-Wadsworth-Emmons reaction The ratio of alkene isomers 5 and 6 is not dependent upon the stereochemical outcome of the initial carbanion addition and upon the ability of the ...
In effect, Hofmann elimination is a retro-Michael addition chemical process. It is important to note here that the physiological process of Hofmann elimination differs from the non-physiological Hofmann degradation process: the latter is a chemical reaction in which a quaternary ammonium hydroxide solid salt is heated to 100 °C, or an aqueous ...