Cyclohexanedione oximes

A Inhibition of acetyl CoA carboxylase (ACCase) Aryloxyphenoxy- propionates Cyclohexanediones oximes 1... 

Acetaldehyde can be isolated and identified by the characteristic melting points of the crystalline compounds formed with hydrazines, semicarbazides, etc these derivatives of aldehydes can be separated by paper and column chromatography (104,113). Acetaldehyde has been separated quantitatively from other carbonyl compounds on an ion-exchange resin in the bisulfite form the aldehyde is then eluted from the column with a solution of sodium chloride (114). In larger quantities, acetaldehyde may be isolated by passing the vapor into ether, then saturating with dry ammonia acetaldehyde—ammonia crystallizes from the solution. Reactions with bisulfite, hydrazines, oximes, semicarb azides, and 5,5-dimethyl-1,3-cyclohexanedione [126-81 -8] (dimedone) have also been used to isolate acetaldehyde from various solutions. 

Ozonolysis of the O-methyl oximes of cyclic ketones in the presence of 1,4-cyclohex-anedione and ozonolysis of the O-methylated dioxime of 1,4-cyclohexanedione in the presence of cyclic ketones afforded the corresponding diozonides . 

The mixed hydrazones (667), prepared from diacetyl monobenzoyl hydrazone and arylhydrazines, undergo oxidative cyclization to 2-aryl-jV-benzoyl-4,5-dimethyl-l,2,3-triazol-l-ylimines (668) in 32-76% yield upon treatment with lead tetraacetate in acetonitrile (Scheme 132) <92JOC2252>. The cychzation of bishydrazones to 1,2,3-triazoles can also occur in acidic or basic media. For instance, the tetrahydrobenzo[ /]triazol-4-one (669) is prepared by the base-catalyzed cyclization of the corresponding a-hydrazono oxime (Equation (53)) <85HCA1748>. 3-Methyl-1,2-cyclohexanedione reacts... 

B. 1,2-Cyclohexanedionedioxime has been prepared by oxi-mating 1,2-cyclohexanedione with hydroxylammonium chloride in aqueous potassium hydroxide solution 3 6 by oximating 2-iso-nitrosocyclohexanone with hydroxylammonium chloride 7 8 and by oximating sodium 2-isonitrosocyclohexanone with hydroxylammonium chloride in methanolic solution.6... 

First, one had to check that the mechanism of action was correct. The product of co-ozonlysis of O-methyl-2-adamantanone oxime with 1,4-cyclohexanedione afforded on treatment with ferrous acetate a secondary carbon-centered free radical that was trapped with the usual spin trap, 2,2,6,6-tetramethylpiperidine-Ar-oxide (TEMPO), and involved a /3-scission of the adamantane fragment, thus proving that the attack of the Fe(ll) species occurred on the less-hindered peroxide bond oxygen atom (Scheme 85) <2004NAT900, 2005JOC513>. 

Ozonolysis. Ozonolysis of cyclohexanone O-methyl oxime 163 in the presence of 1,4-cyclohexanedione 164 gave a complex reaction mixture containing hydroxylamines 164, as a main product (Scheme 71 <1997T5463>). 

The oximes of ketones with large hydrocarbon radicals like the acetyl-phenanthrenes are readily prepared by die action of hydroxylamine hydrochloride in the presence of pyridine. Special studies have been made for the synthesis of 1,2-cyclohexanedione dioxime as well as the next higher homolog. Dimethylglyoxime, CH,C(=NOH)C(=NOH)CH is... 

The dioxime of a cyclic 1,2-diketone (prepared in this example by successive nitrosation and oximation of the 1,3-cyclohexanedione) is oxidized to a furoxan (l,2,S-oxadiazole 2-oxide) the isomeric N-oxide is formed by mild treatment of the dioxime with thionyl chloride [2496]. 

A detailed mechanistic study of the iron-templated reaction of 1,2-cyclohexanedione dioxime (37) with H3BO3 to form complexes of the cage ligand (38) has been reported. The first step appears to be the formation of the /w(oxime) complex, followed by a reversible association with H3BO3 and... 

---