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N-Chlorosuccinimide (NCS) is the organic compound with the formula C 2 H 4 (CO) 2 NCl. This white solid is used for chlorinations. [2] It is also used as a mild oxidant. [3] NCS is related to succinimide, but with N-Cl in place of N-H. The N–Cl bond is highly reactive, and NCS functions as a source of "Cl +".
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
Treatment of imides with halogens and base gives the N-halo derivatives. Examples that are useful in organic synthesis are N-chlorosuccinimide and N-bromosuccinimide, which respectively serve as sources of "Cl +" and "Br +" in organic synthesis.
Other two-electron terminal oxidants used with TEMPO include mCPBA (secondary oxidation is favored, although side reactions may occur), [18] N-chlorosuccinimide, [19] and Oxone. [20] Copper(II), both as the free chloride salt and as a complex with bidentate ligands, oxidizes TEMPO to its oxoammonium salt.
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)
The necessary α-halo sulfones are accessible through oxidation of the corresponding α-halo sulfides with peracids such as meta-chloroperbenzoic acid; oxidation of sulfides takes place selectively in the presence of alkenes and alcohols. α-Halo sulfides may in turn be synthesized through the treatment of sulfides with halogen electrophiles such as N-chlorosuccinimide or N-bromosuccinimide.
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.
The intermediate 4 can also be prepared from dimethyl sulfide and N-chlorosuccinimide (the Corey–Kim oxidation). In some cases, the use of triethylamine as the base can lead to epimerisation at the carbon alpha to the newly formed carbonyl. Using a bulkier base, such as diisopropylethylamine, can mitigate this side reaction.