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Struktur und Solvolyse der Bicyclo[2,2,2]octadin-(2,5)-dibromide. Bicyclo[2,2,2]octan-Reihe. 3. Mitteilung

✍ Scribed by A. Gagneux; C. A. Grob

Publisher
John Wiley and Sons
Year
1959
Tongue
German
Weight
760 KB
Volume
42
Category
Article
ISSN
0018-019X

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✦ Synopsis

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).

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