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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] The trans isomer is selectively trapped as a complex with silver nitrate (in this diagram the trans form looks like a cis form, but see the trans-cyclooctene article for better images):
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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.
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.
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 ...
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.
In organic chemistry, regioselectivity is the preference of chemical bonding or breaking in one direction over all other possible directions. [1] [2] It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will be added.