A new method for mixed halogenation. N-chloroamine - phosphorus bromide system as a synthetic equivalent of the mixed halogen Cl+Br-

Article abstract of DOI:10.1080/10426509808035682

A new method for the mixed halogenation of alkenes has been proposed based on the reaction of olefins with N-chloroamines in the presence of phosphorus bromide or oxybromide. The plausible reaction mechanism and the results of reactions with a number of model unsaturated compounds such as cyclohexene, 1-heptene, ethyl cinnamate, norbornene and those from the bicyclo[2.2.1]heptane series are discussed. In the reactions with reactive olefins this reagent acts as a synthetic equivalent of the unknown mixed halogen [Cl⁺Br^-] with abnormal polarity of halogen atoms. The same reactions activated by PCl₃ or POCl₃ result in dichlorides in yields near to quantitative.

Full text of DOI:10.1080/10426509808035682

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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A NEW METHOD FOR MIXED
HALOGENATION. N-CHLOROAMINE-
PHOSPHORUS BROMIDE SYSTEM AS A
SYNTHETIC EQUIVALENT OF THE MIXED
+
-
HALOGEN Cl Br
a
a
a
Nikolai V. Zyk , Elena K. Beloglazkina , Vladimir S. Tyurin & Nikolai
a
S. Zefirov
a
Department of Chemistry , Moscow State University , Moscow, 119899,
Russia
Published online: 16 Feb 2007.
To cite this article: Nikolai V. Zyk , Elena K. Beloglazkina , Vladimir S. Tyurin & Nikolai S. Zefirov (1998)
A NEW METHOD FOR MIXED HALOGENATION. N-CHLOROAMINE-PHOSPHORUS BROMIDE SYSTEM AS A
+
-
SYNTHETIC EQUIVALENT OF THE MIXED HALOGEN Cl Br , Phosphorus, Sulfur, and Silicon and the Related
Elements, 139:1, 107-122, DOI: 10.1080/10426509808035682
To link to this article: http://dx.doi.org/10.1080/10426509808035682
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