Taylor & Francis
Phosphorus, Sulfur and Silicon and the Related Elements
,  volume 139 ,  issue 1 ,  pages 107-122

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

Publication type: Journal Article
Publication date: 1998-08-01
Taylor & Francis
scimago Q4
wos Q3
SJR: 0.264
CiteScore: 2.6
Impact factor: 1.6
ISSN: 10426507, 15635325, 10267719
Organic Chemistry
Biochemistry
Inorganic Chemistry
Abstract
Abstract 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, norbomene 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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Zyk N. V. et al. 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. 1998. Vol. 139. No. 1. pp. 107-122.
GOST all authors (up to 50) Copy
Zyk N. V., Beloglazkina E. K., Tyurin V. S., Zefirov N. S. 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. 1998. Vol. 139. No. 1. pp. 107-122.
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TY - JOUR
DO - 10.1080/10426509808035682
UR - https://www.tandfonline.com/doi/full/10.1080/10426509808035682
TI - A new method for mixed halogenation. N-chloroamine - phosphorus bromide system as a synthetic equivalent of the mixed halogen Cl+Br-
T2 - Phosphorus, Sulfur and Silicon and the Related Elements
AU - Zyk, Nikolai V.
AU - Beloglazkina, Elena K.
AU - Tyurin, Vladimir S
AU - Zefirov, Nikolai S.
PY - 1998
DA - 1998/08/01
PB - Taylor & Francis
SP - 107-122
IS - 1
VL - 139
SN - 1042-6507
SN - 1563-5325
SN - 1026-7719
ER -
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@article{1998_Zyk,
author = {Nikolai V. Zyk and Elena K. Beloglazkina and Vladimir S Tyurin and Nikolai S. Zefirov},
title = {A new method for mixed halogenation. N-chloroamine - phosphorus bromide system as a synthetic equivalent of the mixed halogen Cl+Br-},
journal = {Phosphorus, Sulfur and Silicon and the Related Elements},
year = {1998},
volume = {139},
publisher = {Taylor & Francis},
month = {aug},
url = {https://www.tandfonline.com/doi/full/10.1080/10426509808035682},
number = {1},
pages = {107--122},
doi = {10.1080/10426509808035682}
}
MLA
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Zyk, Nikolai V., et al. “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, vol. 139, no. 1, Aug. 1998, pp. 107-122. https://www.tandfonline.com/doi/full/10.1080/10426509808035682.