N-Chlorosuccin imide

Oxidation of tertiary amines with N-chloronylon 6,6 has also been investigated in several solvents Thus, N-chloronylon has been found to oxidize N J -dimethyl-aniline at room temperature to N-methylaniline in 15—50% yield, depending on the solvent used. The oxidation of NJM-dimethylbenzylamine gives benzddehyde in 15-30% yield and a small amount of N-methylbenzylamine. A comparison of these oxidations with those using the low molecular wei t analoges, e. g. N-chlorosuccin-imide, indicates that in both cases the reaction paths are similar. However, the poor yields observed in these oxidations of amines make these polymeric oxidizing agents unsuitable for amine oxidations. 

Only a few modifications of mycinose itself, on either demycarosyltylosin or mycinamicin, have been reported. The 4"-hydroxyl was readily oxidized to the ketone with DCC and DMSO or with diisopropylsulfide and N-chlorosuccin-imide [131, 133] however, attempts at conventional reductive amination resulted in cleavage of mycinose instead [130, 133]. Since reduction of the 4"-oxime produced an imine which was unstable toward hydrolysis back to the ketone, a convenient method for one-step reduction of the 4"-oxime to the 4"-amino derivative using TiCl3 and NaBH3CN was devised [133]. lodination at 4" by methyl triphenoxyphosphonium iodide has been observed as a side reaction subsequent elimination of HI yielded a 3",4"-anhydro derivative [134]. It should also be noted that a number of structural variations in this saccharide already exist due to the compounds isolated from the mutant strains of these macrolide-producing organisms [70, 75, 135]. 

The spin trapping method has also been applied to the detection and identification of intermediate primary radicals produced from initiator systems such as triethyl-borane/oxygen benzoyl peroxide/N,N-dimethylaniline and N-chlorosuccin-imide/p-toluenesulfonic acid , and provided important information on the generation of free radicals in initiator systems. 

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