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Hofmann elimination provided precisely this basis: It is a chemical process in which a suitably activated quaternary ammonium compound can be degraded by the mildly alkaline conditions present at physiological pH and temperature. [54] In effect, Hofmann elimination is a retro-Michael addition chemical process.
The Cope elimination is very similar to the Hofmann elimination in principle, but occurs under milder conditions. It also favors the formation of the Hofmann product, and for the same reasons. [3] An example of a Hofmann elimination (not involving a contrast between a Zaitsev product and a Hofmann product) is the synthesis of trans-cyclooctene. [4]
In the development of atracurium the main idea was to make use of Hofmann elimination of the muscle relaxant in vivo. 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.
Because Hofmann elimination is a temperature- and plasma pH-dependent process, cisatracurium's rate of degradation in vivo is highly influenced by body pH and temperature just as it is with the parent molecule, atracurium: thus, an increase in body pH favors the elimination process, [citation needed] whereas a decrease in temperature slows down ...
In order for the Hofmann product to form, elimination must occur at the 6-position. Because the proton at this position has the correct orientation relative to the leaving group, elimination can and does occur. As a result, this particular reaction produces only the Hofmann product.
In order to determine the structural and geometrical factors affecting the intramolecular hydrogen atom transfer, a number of different N-chloroamines were examined in the Hofmann–Löffler–Freytag reaction. The systems were judiciously chosen in order to obtain data on the following points: relative migration tendencies of primary (1 ...
The reaction mechanism of the Stevens rearrangement is one of the most controversial reaction mechanisms in organic chemistry. [4] Key in the reaction mechanism [5] [6] for the Stevens rearrangement (explained for the nitrogen reaction) is the formation of an ylide after deprotonation of the ammonium salt by a strong base.
Quinine's vinyl group is then constructed by Hofmann elimination with sodium hydroxide in water at 140 °C. This process is accompanied by hydrolysis of both the ester and the amide group but it is not the free amine that is isolated but the urea 14 by reaction with potassium cyanate .