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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 ...
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 ...
The CBS reduction has proven to be an effective and powerful method to reduce a wide range of different types of ketones in both a stereoselective and chemoselective manner. Substrates include a large variety of aryl-aliphatic, di-aliphatic, di-aryl, α,β unsaturated enone and ynone systems, as well as ketones containing heteroatoms.
A key iodine(III) enolate intermediate forms, which then undergoes either nucleophilic substitution (α-functionalization), elimination (dehydrogenation), or rearrangement. Common hypervalent iodine reagents used to effect these transformations include iodosylbenzene (PhIO), [ 1 ] Koser's reagent (PhI(OTs)OH), [ 1 ] and (dichloroiodo)benzene ...
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 ...
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.
The Buchner–Curtius–Schlotterbeck reaction is the reaction of aldehydes or ketones with aliphatic diazoalkanes to form homologated ketones. [1] It was first described by Eduard Buchner and Theodor Curtius in 1885 [2] and later by Fritz Schlotterbeck in 1907. [3]
A typical rearrangement reaction is that between the aldose glyceraldehyde and the ketose dihydroxyacetone in a chemical equilibrium. The Lobry de Bruyn–Van Ekenstein transformation is relevant for the industrial production of certain ketoses and was discovered in 1885 by Cornelis Adriaan Lobry van Troostenburg de Bruyn and Willem Alberda van ...