Scientific article

Reaction of 2-Methylenenorbornane with N-Bromosuccinimide

Published inHelvetica chimica acta, vol. 55, no. 6, p. 2244-2252
Publication date1972-07-10

The reaction of 2-methylenenorbornane with N-bromosuccinimide produced a mixture of six monobromides in an overall yield of about 60%. By irradiation in the presence of benzoyl peroxide exo- and endo-3-bromo-2-methylenenorbornanes, 2-bromomethylnorborn-2-ene, Z- and E-2-bromomethylenenorbornanes and 1-bromomethylnortricyclene were found in a percentage ratio of 43.0, 7.5, 6.5, 19.0, 19.0 and 5.0. Without benzoyl peroxide, in the dark, the same products were obtained, but in a percentage ratio of 23.0, 3.0, 17.0, 26.0, 26.0 and 7.0. These results are rationalized in terms of an ionic mechanism in concurrence with some radical mechanism contribution.

Citation (ISO format)
JEFFORD, Charles, WOJNAROWSKI, W. Reaction of 2-Methylenenorbornane with N-Bromosuccinimide. In: Helvetica chimica acta, 1972, vol. 55, n° 6, p. 2244–2252. doi: 10.1002/hlca.19720550647
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Article (Published version)
ISSN of the journal0018-019X

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