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N-Chlorinations

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The reagents poly(N,N'-dichloro-N-ethylbenzene-1,3-disulfonamide) (PCBS) and N,N,N',N'-tetrachlorobenzene-1,3-disulfonamide (TCBDA) allow the preparation of N,N-dichloroamines, nitriles, and aldehydes from primary amines. A direct oxidative conversion of primary alcohols into nitriles was successfully carried out in aqueous ammonia.
R. Ghorbani-Vaghei, H. Veisi, Synthesis, 2009, 945-950.


The combination of phthaloyl peroxide with commercially available halide salts provides an unique halogenating system for Hofmann-Löffler-Freytag-type reactions to produce N-chloroamides, δ-brominated products, and even biologically relevant pyrrolidines under mild conditions in good yields.
D. Chang, R. Zhao, C. Wei, Y. Yao, Y. Liu, L. Shi, J. Org. Chem., 2018, 83, 3305-3315.


N-Chlorination of various amides, carbamates and lactams with inexpensive and stable calcium hypochlorite on moist alumina proceeds smoothly and efficiently. Excellent results were also observed for the N-chlorination of protected amino acid esters with a cyclopropane moiety.
O. V. Larionov, S. I. Kozhushkov, A. de Meijere, Synthesis, 2003, 1916-1919.