N-Chlorinations
Recent Literature
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.