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Several reagents can be substituted for bromine. Sodium hypochlorite, [4] lead tetraacetate, [5] N-bromosuccinimide, and (bis(trifluoroacetoxy)iodo)benzene [6] can effect a Hofmann rearrangement. The intermediate isocyanate can be trapped with various nucleophiles to form stable carbamates or other products rather than undergoing decarboxylation.
In chemistry, the haloform reaction (also referred to as the Lieben haloform reaction) is a chemical reaction in which a haloform (CHX 3, where X is a halogen) is produced by the exhaustive halogenation of an acetyl group (R−C(=O)CH 3, where R can be either a hydrogen atom, an alkyl or an aryl group), in the presence of a base.
HC≡CH + KOH ⇌ HC≡CK + H 2 O; RR'C=O + HC≡CK ⇌ RR'C(OK)C≡CH; The metal acetylide then reacts with an aldehyde or ketone to form a propargyl alcohol. When an α-hydrogen is present (as is the case when the carbonyl is an aldehyde), it will tautomerize to the corresponding enone. [4]
Structure of N-bromosuccinimide, a common brominating reagent in organic chemistry. Like the other carbon–halogen bonds, the C–Br bond is a common functional group that forms part of core organic chemistry. Formally, compounds with this functional group may be considered organic derivatives of the bromide anion.
Structure of N-bromosuccinimide, a common brominating reagent in organic chemistry. Like the other carbon–halogen bonds, the C–Br bond is a common functional group that forms part of core organic chemistry. Formally, compounds with this functional group may be considered organic derivatives of the bromide anion.
Halogenation of α,β-unsaturated ketone [3]. On α,β-Unsaturated ketones or enones, it's possible to halogenate with iodine selectively on the more saturated alpha on the ketone selectively over the unsaturated side.
Cyanogen bromide is a common reagent in organic synthesis. In most reactions, it acts as a source of electrophilic cyanogen and nucleophilic bromide; carbocations preferentially attack the nitrogen atom. [4] In the presence of a Lewis acid, it cyanidates arenes. [9] BrCN converts alcohols to cyanates; amines to cyanamides or dicyanamides. [4]
An example of the Hell–Volhard–Zelinsky reaction can be seen in the preparation of alanine from propionic acid.In the first step, a combination of bromine and phosphorus tribromide is used in the Hell–Volhard–Zelinsky reaction to prepare 2-bromopropionic acid, [3] which in the second step is converted to a racemic mixture of the amino acid product by ammonolysis.
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