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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.
Several reagents can be substituted for bromine. Sodium hypochlorite, [4] lead tetraacetate, [5] N-bromosuccinimide, and (bis(trifluoroacetoxy)iodo)benzene [6] can affect a Hofmann rearrangement. The intermediate isocyanate can be trapped with various nucleophiles to form stable carbamates or other products rather than undergoing decarboxylation.
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.
Unsolved Problems in Nanotechnology: Chemical Processing by Self-Assembly - Matthew Tirrell - Departments of Chemical Engineering and Materials, Materials Research Laboratory, California NanoSystems Institute, University of California, Santa Barbara [No doc at link, 20 Aug 2016]
Chemical formula. C 4 H 5 N O 2: Molar mass: 99.089 g·mol −1 Appearance ... N-Bromosuccinimide; References This page was last edited on 25 October 2024, at 15:33 ...
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.