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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.


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.