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Reaktion von (Z,Z)-1,5-Cyclononadien mit N-Bromsuccinimid in Gegenwart von Wasser oder Methanol |
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| Authors: | Dr Günter Haufe Manfred Mühlstädt Jürgen Graefe |
| Institution: | (1) Sektion Chemie, Karl-Marx-Universität Leipzig, Liebigstraße 18, DDR-701 Leipzig, Deutsche Demokratische Republik;(2) Sektion Chemie, Friedrich-Schiller-Universität Jena, Deutsche Demokratische Republik |
| Abstract: | The action of N-bromosuccinimide (NBS) and water on (Z,Z)-1,5-cyclononadiene (1) results in transanular reactions to give 1 -bromo-3a  ,4,5,6,7,7a -hexahydroindan-4-ol (2 a) and 2,6-dibromo-10-oxabicyclo5.2.1]decane (3). The formation of2 a is a result of transanular double bond participation.3 is considered to be produced from intermediary (Z)-2-bromo-5-cyclononen-1-ol (6)via transanular participation of the hydroxyl group. The reaction of1 withNBS and methanol similarly produces 1-bromo-4-methoxy-3a,4,5,6,7,7a -hexahydroindan (2 b) and3.3. Mitt.:G. Haufe, M. Mühlstädt undJ. Graefe, Mh. Chem.108, 199 (1977). Aus der Dissertation zur Promotion A,G. Haufe, Karl-Marx-Universität Leipzig, 1975. |
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