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α-Halo ketones can react with amines to form an α-halo imine, which can be converted back to the parent halo ketone by hydrolysis, so that halo imines may be used as masked versions of halo ketones. This allows some chemical transformations to be achieved that are not possible with the parent halo ketones directly.
The reduction of α-halo ketones generates a variety of product structures that may exhibit unique substitution patterns and reactivity. For instance, reduction of α,α'-dihalo ketones leads to 2-oxyallyl metal complexes, which participate in [4+3] and [3+2] cycloaddition reactions as the 2π component.
The Reformatsky reaction (sometimes transliterated as Reformatskii reaction) is an organic reaction which condenses aldehydes or ketones with α-halo esters using metallic zinc to form β-hydroxy-esters: [1] [2] The Reformatsky reaction. The organozinc reagent, also called a 'Reformatsky enolate', is prepared by treating an alpha-halo ester ...
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 ...
The Darzens reaction (also known as the Darzens condensation or glycidic ester condensation) is the chemical reaction of a ketone or aldehyde with an α-haloester in the presence of a base to form an α,β-epoxy ester, also called a "glycidic ester". [1] [2] [3] This reaction was discovered by the organic chemist Auguste Georges Darzens in 1904 ...
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In a related reaction, α-halo carboxylic esters can be reduced by lithium aluminium hydride to the α-halo alcohols, which can be converted to the α-epoxides. [5] α-Halo-esters can be converted to vinyl halides. upon reaction with ketones and chromous chloride. [6]
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