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Categories: C-Cl Bond Formation, C-N Bond Formation > Amines

Synthesis of 1,2-chloroamines

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The use of diphenyl selenide as a Lewis base catalyst enables a mild chloroamidation of a wide rand of olefinic substrates including starting materials with acid labile functional groups.
D. W. Tay, I. T. Tsoi, J. C. Er, G. Y. C. Leung, Y.-Y. Yeung, Org. Lett., 2013, 15, 1310-1313.


A practical, regio- and diastereoselective synthesis of vicinal chloramines from electron-deficient olefins and Chloramine-T is promoted by Brønsted acids in water. This novel protocol is efficient, mild, ecofriendly, and broadly applicable for the aminochlorination of various electron-deficient olefins including α,β-unsaturated ketones, cinnamate, and cinnamide.
X.-L. Wu, G.-W. Wang, J. Org. Chem., 2007, 72, 9398-9401.


The regio- and stereoselective aminochlorination of α,β-unsaturated ketones with N,N-dichloro-p-toluenesulfonamide (4-TsNCl2) and CuOTf as catalyst provides an easy access to vicinal haloamino ketones, with excellent regioselectivity and good yields. Aromatic and aliphatic enones give opposite regioselectivity.
D. Chen, C. Timmons, S. Chao, G. Li, Eur. J. Org. Chem., 2004, 3097-3101.


D. Chen, C. Timmons, S. Chao, G. Li, Eur. J. Org. Chem., 2004, 3097-3101.

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Radical halo-nitration of alkenes proceeds easily by radical addition of nitrogen dioxide generated by thermal decomposition of iron(III) nitrate nonahydrate and subsequent trapping of the resultant radical by a halogen atom in the presence of a halogen salt. Application of this method to synthesis of nitroalkenes is also described.
T. Taniguchi, T. Fuji, H. Ishibashi, J. Org. Chem., 2010, 75, 8126-8132.