Abstract
IT was first shown by Ziegler and co-workers1 that N-bromosuccinimide (XNBr) reacts with cyclohexene to give 3-bromocyclohexene (I) and succinimide. We have found that if the reaction is carried out in chloroform, benzene or petrol solution in the presence of salts such as tetraethylammonium bromide, tetraethylammonium iodide, or triethylamine hydrobromide, 1: 2-dibromocyclohexane (II) is formed instead of 3-bromocycloohexene, in proportions depending on the exact conditions employed. The same effect can be brought about by the addition of small amounts (c. 10 mol. per cent based on N-bromosuccinimide) of triethylamine, which reacts with part of the N-bromosuccinimide to give triethylamine hydrobromide and succinimide.
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References
Ziegler, Späth, Schaaf, Schumann and Winkelmann, Annalen, 551, 80 (1942).
Howton, J. Amer. Chem. Soc., 69, 2060 (1947). Buchmann and Howton, ibid., 70, 2517, 3510 (1948).
Buckles, J. Amer. Chem. Soc., 71, 1157 (1949).
Bloomfleld, J. Chem. Soc., 114 (1944).
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BRAUDE, E., WAIGHT, E. N-Bromosuccinimide as a Reagent for Bromine Addition. Nature 164, 241 (1949). https://doi.org/10.1038/164241a0
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DOI: https://doi.org/10.1038/164241a0
