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Reaktion von (Z,Z)-1,5-Cyclononadien mit N-Bromsuccinimid in Gegenwart von Wasser oder Methanol

Reaction of (Z,Z)-1,5-cyclononadiene with N-bromosuccinimide in the presence of water, and methanol, resp. Transanular reactions of cycloalkadienes and cycloalkatrienes, IV Transanulare Reaktionen von Cycloalkadienen und Cycloalkatrienen, 4. Mitt.

  • Organisches Chemie und Biochemie
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Abstract

The action of N-bromosuccinimide (NBS) and water on (Z,Z)-1,5-cyclononadiene (1) results in transanular reactions to give 1β-bromo-3a α,4α,5,6,7,7a α-hexahydroindan-4-ol (2 a) and 2β,6β-dibromo-10-oxabicyclo[5.2.1]decane (3). The formation of2 a is a result of transanular double bond participation.3 is considered to be produced from intermediary (Z)-2β-bromo-5-cyclononen-1α-ol (6)via transanular participation of the hydroxyl group. The reaction of1 withNBS and methanol similarly produces 1β-bromo-4-methoxy-3aα,4α,5,6,7,7a α-hexahydroindan (2 b) and3.

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Authors and Affiliations

  1. Sektion Chemie, Karl-Marx-Universität Leipzig, Liebigstraße 18, DDR-701, Leipzig, Deutsche Demokratische Republik

    Günter Haufe & Manfred Mühlstädt

  2. Sektion Chemie, Friedrich-Schiller-Universität Jena, Deutsche Demokratische Republik

    Jürgen Graefe

Authors
  1. Günter Haufe
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  2. Manfred Mühlstädt
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  3. Jürgen Graefe
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Additional information

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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Haufe, G., Mühlstädt, M. & Graefe, J. Reaktion von (Z,Z)-1,5-Cyclononadien mit N-Bromsuccinimid in Gegenwart von Wasser oder Methanol. Monatshefte für Chemie 108, 1431–1439 (1977). https://doi.org/10.1007/BF01046458

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