Phosphorus, Sulfur and Silicon and the Related Elements p. 107 - 122 (1998)
Update date:2022-08-17
Topics:
Zyk, Nikolai V.
Beloglazkina, Elena K.
Tyurin, Vladimir S.
Zefirov, Nikolai S.
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.
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