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

Reaction of (Z,Z)-1,5-cyclooctadiene with N-bromosuccinimide in the presence of water, and methanol, resp. transanular reactions of cycloalkadienes and cycloalkatrienes, V

Transanulare Reaktionen von Cycloalkadienen und Cycloalkatrienen, 5. Mitt.

  • Organische Chemie und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

The action of N-bromosuccinimide (NBS) and water on (Z, Z)-1,5-cyclooctadiene (1) results in the formation ofendo,endo-2,5-dibromo-9-oxabicyclo [4.2.1]nonane (2),endo,endo-2,6-dibromo-9-oxabicyclo[3.3.1]nonane (3),trans-6-bromo-(Z)-cycloocten-5-ol (4a),endo-6-bromo-cis-bicyclo[3.3.0]octan-2-ol (5a), andtrans-5,6-dibromo-(Z)-cyclooctene (6).2 and3 are considered to be produced from intermediary4a via transanular participation of the hydroxyl group.5a is formed in a result of transanular double bond participation.

The reaction of1 withNBS and methanol similarly produces2, 3,trans-6-bromo-5-methoxy-(Z)-cyclooctene (4b),endo-6-bromo-2-methoxy-cis-bicyclo-[3.3.0]octane (5b), and6.

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Authors and Affiliations

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

    Günter Haufe, Erich Kleinpeter & Manfred Mühlstädt

  2. Sektion Chemie, Friedrich-Schiller-Universität Jena, DDR-69, Jena, Deutsche Demokratische Republik

    Jürgen Graefe

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

4. Mitt.:G. Haufe, M. Mühlstädt undJ. Graefe, Mh. Chem.108, 1431 (1977).

2 Aus der Dissertation zur Promotion A vonG. Haufe, Karl Marx-Universität Leipzig, 1975.

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Haufe, G., Kleinpeter, E., Mühlstädt, M. et al. Reaktion von (Z,Z)-1,5-Cyclooctadien mit N-Bromsuccinimid in Gegenwart von Wasser oder Methanol. Monatshefte für Chemie 109, 575–585 (1978). https://doi.org/10.1007/BF00912775

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  • DOI: https://doi.org/10.1007/BF00912775

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