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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.
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]
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.
The resultant alkenylalane was cooled to –30°, diluted with 15 mL of dry ether, and treated with 5.35 g (30.1 mmol) of N-bromosuccinimide while keeping the temperature below –15°. The reaction mixture was gradually warmed to room temperature and stirred for 1 hour before being poured slowly into a mixture of 6 N hydrochloric acid (50 mL ...
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]
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.
N-Iodosuccinimide (NIS) is a reagent used in organic chemistry for the iodination of alkenes and as a mild oxidant. [2] NIS is the iodine analog of N-chlorosuccinimide (NCS) and N-bromosuccinimide (NBS) which are used for similar applications.
Photocyclization can be used as the final step of a sequence to generate a fused aromatic ring at a benzylic position. After benzylic bromization with N-bromosuccinimide, transformation to the phosphonium salt, and a Wittig reaction with anaromatic aldehyde, photocyclization fuses the aromatic rings. Iteration of this sequence results in helicenes.