Oximes exist as two stereoisomers: a syn isomer and an anti isomer. Aldoximes, except for aromatic aldoximes, exist only as a syn isomer, while ketoximes can be separated almost completely and obtained as a syn isomer and an anti isomer.
Oximes can also be obtained from reaction of nitrites such as isoamyl nitrite with compounds containing an acidic hydrogen atom. Examples are the reaction of ethyl acetoacetate and sodium nitrite in acetic acid, the reaction of methyl ethyl ketone with ethyl nitrite in hydrochloric acid. and a similar reaction with propiophenone, the reaction of phenacyl chloride, the reaction of malononitrile with sodium nitrite in acetic acid
A conceptually related reaction is the Japp-Klingemann reaction.
In the Neber rearrangement certain oximes are converted to the corresponding alpha-amino ketones.
Oxime compounds are used as antidotes for nerve agents. A nerve agent inactivates acetylcholinesterase molecules by phosphorylation of the molecule. Oxime compounds can reactivate acetylcholinesterate by attaching to the phosphorus atom and forming an oxime-phosphonate which then splits away from the acetylcholinesterase molecule. The most effective oxime nerve-agent antidotes are pralidoxime (also known as 2-PAM), obidoxime, methoxime, HI-6, Hlo-7, and TMB-4. The effectiveness of the oxime treatment depends on the particular nerve agent used. Perillartine, the oxime of perillaldehyde is used as an artificial sweetener in Japan, as it is 2000 times sweeter than sucrose. Salicylaldoxime is a chelator.
A novel design strategy for blocked isocyanates to enhance their reactivity with alcohols. Oxime blocking agents which undergo intramolecular cyclization.
Feb 01, 1992; Previous studies have established that the reaction of alcohols and amines with oxime-blocked isocyanates occurs by a...
Reactivation of sarin-inhibited pig brain acetylcholinesterase using oxime antidotes.(Toxicology Investigations)(Clinical report)
Dec 01, 2006; ABSTRACT Introduction: Organophosphorus nerve agents inhibit the enzyme, acetylcholinesterase (AChE; EC 126.96.36.199). AChE...
Discussion of "efficient, microwave-assisted intramolecular 1,3-dipolar cycloadditions of oximes and N-methylnitrones derived from o-alkenylmethoxyacetophenones" (1).(DISCUSSION)
Jul 01, 2006; The following discussion note arises in defence of comments and assertions made upon our work (1) in the paper entitled...