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Synthesis of 1,2-chloroamines


Recent Literature

Tetrabutylammonium fluoride promotes ring-opening reactions of aziridines with trimethylsilyl compounds to give the corresponding products regioselectively in excellent yield. This reaction provides a facile and efficient access to cyano-, azido-, or chloroamines. The products are easily transformed to vicinal diamines or β-amino acids.
J. Wu, X.-L. Hou, L.-X. Dai, J. Org. Chem., 2000, 65, 1344-1348.

Aziridines are opened regioselectively with hydrogen and lithium halides to yield β-haloamines in the presence of β-cyclodextrin using water as the solvent.
N. S. Krishnaveni, K. Surendra, M. Narender, Y. V. D. Nageswar, K. R. Rao, Synthesis, 2004, 501-502.

An aminohalogenation of cinnamic esters with N,N-dichloro-p-toluenesulfonamide provides vicinal chloroamine derivatives in very good yields. The reaction was performed in MeCN using ZnCl2 or Cu(OTf)2 as catalyst. The stereochemistry was unambiguously determined by transforming one of the products to a known sample.
G. Li, H.-X. Wei, S. H. Kim, M. Neighbors, Org. Lett., 1999, 1, 395-397.