Hofmann elimination

The mechanism is similar to that of the Hofmann elimination.

This organic reaction gives the same result as the Hofmann elimination, but the base is a part of the leaving group.

In effect, Hofmann elimination is a retro-Michael addition chemical process.

Competing reactions are the Sommelet-Hauser rearrangement and the Hofmann elimination.

Vinylacetylene was first prepared by Hofmann elimination of the related quaternary ammonium salt:

The Hofmann rearrangement and Hofmann elimination reaction bear his namesake.

The Cope elimination is very similar to the Hofmann elimination in principle, but occurs under milder conditions.

In the Hofmann elimination, the least substituted alkene is typically favored due to intramolecular steric interactions.

One approach towards improving the chemical stability towards Hofmann elimination is to remove all β-hydrogens at the cationic site.

These intramolecular interactions are relevant to the distribution of products in the Hofmann elimination reaction, which converts amines to alkenes.

The Hofmann elimination is unusual in that the less substituted (non-Saytseff) alkene is usually the major product.

Subsequent ester hydrolysis of the monoacrylate generates the monoquaternary alcohol, although the rate-liminting step is Hofmann elimination.

Atracurium is susceptible to degradation by Hofmann elimination and ester hydrolysis as components of the in vivo metabolic processes.

The latter compound can be synthesized from p-xylene involving several steps involving bromination, amination and Hofmann elimination.

In the development of atracurium the main idea was to make use of Hofmann elimination of the muscle relaxant in vivo.

See the atracurium page for information on Hofmann elimination in vivo versus the Hofmann degradation chemical reaction.

This reaction is also sometimes called the Hofmann degradation or the Harmon Process, and should not be confused with the Hofmann elimination.

One of the metabolites of cistracurium via Hofmann elimination is laudanosine - see the atracurium page for further discussion of the issue regarding this metabolite.

Laudanosine is also a metabolite of cisatracurium that, because of its identical structure to atracurium, undergoes chemodegradation via Hofmann elimination in vivo.

Starting from cyclooctene oxide, trans-2-Aminocyclooctanol gives a mixture of Cyclooctenimine and of cyclooctanone as a result of competing Hofmann elimination.

Attempted isolation of pure BuNOH induces Hofmann elimination, leading to BuN and 1-butene.

In vitro studies using human plasma indicated that cisatracurium spontaneously degrades at physiological pH via Hofmann elimination to yield laudanosine and the quaternary monoacrylate.

Examples are eliminations involving the Burgess reagent, Hofmann elimination (with some sterically hindered substrates), the Cope elimination and ester pyrolysis.

When working with bisbenzyl-isoquinolinium types of molecules, inserting proper features into the molecule such as an appropriate electron withdrawing group then Hofmann elimination should occur at conditions in vivo.

Two selected methods for the synthesis of tropone are by selenium dioxide oxidation of cycloheptatriene and indirectly from tropinone by a Hofmann elimination and a bromination.