Struktur und Solvolyse der Bicyclo[2,2,2]octadin‐(2,5)‐dibromide. Bicyclo[2,2,2]octan‐Reihe. 3. Mitteilung
- 1 January 1959
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 42 (6) , 1753-1764
- https://doi.org/10.1002/hlca.19590420602
Abstract
The bromination of bicyclo[2.2.2]octadiene‐(2,5) (1) leads to a mixture of trans‐2,3‐dibromo‐bicyclo[2.2.2]octene‐(5) (9) and trans‐3,5‐dibromo‐homotricyclene (7a) in the ratio 7:3. This result is explained by endo addition of bromine to (1) with formation of an intermediate homoallylic ion (23) or, possibly, the unusual symmetrical bridged bromonium ion (24).Keywords
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