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The Wohl–Ziegler reaction [1] [2] is a chemical reaction that involves the allylic or benzylic bromination of hydrocarbons using an N-bromosuccinimide and a radical initiator. [3] Best yields are achieved with N-bromosuccinimide in carbon tetrachloride solvent. Several reviews have been published. [4] [5]
N-Bromosuccinimide or NBS is a chemical reagent used in radical substitution, electrophilic addition, and electrophilic substitution reactions in organic chemistry. NBS can be a convenient source of Br • , the bromine radical.
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.
This compound is also the starting material for the dibromide through N-bromosuccinimide (NBS) and silver nitrate: Cadiot–Chodkiewicz coupling application. The coupling reaction itself takes place in methanol with piperidine, the hydrochloric acid salt of hydroxylamine and copper(I) bromide. [3]
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.
Free-radical reactions depend on one or more relatively weak bonds in a reagent. Under reaction conditions (typically heat or light), some weak bonds homolyse into radicals, which then induce further decomposition in their compatriots before recombination. Different mechanisms typically apply to reagents without such a weak bond.
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.
Succinimides refers to compounds that contain the succinimide group. These compounds have some notable uses. Several succinimides are used as anticonvulsant drugs, including ethosuximide, phensuximide, and methsuximide.