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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. [1]
Dimethyl sulfide (Me 2 S) is treated with N-chlorosuccinimide (NCS), resulting in formation of an "active DMSO" species that is used for the activation of the alcohol. Addition of triethylamine to the activated alcohol leads to its oxidation to aldehyde or ketone and generation of dimethyl sulfide. In variance with other alcohol oxidation using ...
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.
Bromine itself can be used, but due to its toxicity and volatility, safer brominating reagents are normally used, such as N-bromosuccinimide. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution. [15]
Bromine itself can be used, but due to its toxicity and volatility, safer brominating reagents are normally used, such as N-bromosuccinimide. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution. [51]
C 4 H 5 N O 2: Molar mass: 99.089 g·mol −1 Appearance White crystalline powder Density: 1.41 g/cm 3: Melting point: 125 to 127 °C (257 to 261 °F; 398 to 400 K) Boiling point: 287 to 289 °C (549 to 552 °F; 560 to 562 K)
Skraup reaction; Smiles rearrangement; S N Ar nucleophilic aromatic substitution; S N 1; S N 2; S N i; Solvolysis; Sommelet reaction; Sonn–Müller method; Sonogashira coupling; Sørensen formol titration; Staedel–Rugheimer pyrazine synthesis; Stahl oxidation; Staudinger reaction; Staudinger synthesis; Steglich esterification; Stephen ...