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Vicarious nucleophilic substitution of hydrogen in nitro-1,6-methano[10]annulenes

Vicarielle nucleophile Substitution von Wasserstoff in Nitro-1,6-methano[10]annulenen

  • Organisch Chemie Und Biochemie
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Summary

The 2- and 3-nitro-1,6-methano[10]annulenes and their 11,11-difluoro derivatives react with carbanions bearing leaving groups at the carbanionic center according to the Vicarious Nucleophilic Substitution of Hydrogen (VNS) scheme. The analogy between corresponding annulenes and naphthalenes with respect to reactivity is discussed.

Zusammenfassung

2- und 3-Nitro-1,6-methano[10]annulene und ihre 11,11-Difluoroderivate reagieren mit Carbanionen, die am carbanionischen Zentrum Abgangsgruppen aufweisen, nach dem Schema der vicariellen nucleophilen Substitution (VNS). Die Analogie zwischen entsprechenden Annulenen und Naphthalinen bezüglich ihrer Reaktivität wird diskutiert.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Polish Academy of Sciences, PL-01224, Warszawa, Poland

    S. Ostrowski & B. Mudryk

  2. Institut für Organische Chemie, Universität Köln, D-50939, Köln, Federal Republic of Germany

    R. J. Moritz

Authors
  1. S. Ostrowski
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  2. R. J. Moritz
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  3. B. Mudryk
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Ostrowski, S., Moritz, R.J. & Mudryk, B. Vicarious nucleophilic substitution of hydrogen in nitro-1,6-methano[10]annulenes. Monatsh Chem 126, 447–459 (1995). https://doi.org/10.1007/BF00813207

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  • DOI: https://doi.org/10.1007/BF00813207

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