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Struktur und Solvolyse der Bicyclo[2,2,2]octadin‐(2,5)‐dibromide. Bicyclo[2,2,2]octan‐Reihe. 3. Mitteilung
Author(s) -
Gagneux A.,
Grob C. A.
Publication year - 1959
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19590420602
Subject(s) - chemistry , bicyclic molecule , halogenation , bromine , medicinal chemistry , stereochemistry , organic chemistry
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).