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Synthesis of 1,2-chloroamines
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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.