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This rearrangement differs from similar isomerizations of carbohydrates, which involve the migration of hydrogen and proceed through discrete enediol intermediates.These include the Lobry–de Bruyn–van Ekenstein transformation, [2] the Heyns [3] and Amadori rearrangements, [4] and the Voight [5] and Bilik [6] reactions. α-hydroxy imines may also undergo the rearrangement, although the ...
α-hydroxy ketones give positive Tollens' and Fehling's test. Some acyloins rearrange with positions swapped under the influence of base in the Lobry–de Bruyn–van Ekenstein transformation; A similar reaction is the so-called Voigt amination [6] where an acyloin reacts with a primary amine and phosphorus pentoxide to an α-keto amine: [7]
This property is exploited in the Favorskii rearrangement, where base abstracts first an acidic α-hydrogen and the resulting carbanion then displaces the halogen. In crossed aldol reactions between halo ketones and aldehydes, the initial reaction product is a halohydrin which can subsequently form an oxirane in the presence of base.
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In the case of cyclic α-halo ketones, the Favorskii rearrangement constitutes a ring contraction. This rearrangement takes place in the presence of a base, sometimes hydroxide , to yield a carboxylic acid, but usually either an alkoxide base or an amine to yield an ester or an amide , respectively. α,α'-Dihaloketones eliminate HX under the ...
Organocuprates may also be employed for the reduction of α,α'-dihalo ketones to alkylated ketones. In the absence of an electrophile the monoalkyl ketone is isolated in good yield; [18] when an alkyl iodide is added, the dialkyl ketone is isolated (geminal alkylation is a problematic side reaction). [19] (10)
The usual way of doing this is from the relevant oxime, via the Neber rearrangement. [ 5 ] [ 6 ] The original Knorr synthesis employed two equivalents of ethyl acetoacetate , one of which was converted to ethyl 2-oximinoacetoacetate by dissolving it in glacial acetic acid , and slowly adding one equivalent of saturated aqueous sodium nitrite ...
Alpha- and beta-hydroxy ketones. In organic chemistry, a hydroxy ketone (often referred to simply as a ketol) is a functional group consisting of a ketone (>C=O) flanked by a hydroxyl group (−OH). Chemicals in this group can be classified by the position of the hydroxyl relative to the ketone.