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Structure of a ring enlarged product from the base induced rearrangement of dibromomethylenebenzonorbornene

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Abstract

The base-catalyzed rearrangement reactions of 2-bromomethylenebenzonorbornene8 and 2,2-dibromomethylenebenzonorbornene9 were studied. Reaction of8 with potassiumtert-butoxide in THF gave only the enol ether11 whose formation is rationalized via a carbene-cycloalkyne mechanism. However, treatment of9 with phenyllithium in THF at −40°C gave the ringenlarged dibromide13 whose structure is reported herein. The ring-enlarged product13 is rationalized in terms of carbanionic rearrangement. Quantum mechanical calculations are consistent with these observations.

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Authors and Affiliations

  1. Department of Chemistry, Atatürk University, 25240, Erzurum, Turkey

    Metin Balci & Yavuz Ta§kesenligil

  2. Department of Chemistry, Texas Christian University, 76129, Fort Worth, Texas

    Mariusz Krawiec & William H. Watson

Authors
  1. Metin Balci
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  2. Mariusz Krawiec
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  3. Yavuz Ta§kesenligil
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  4. William H. Watson
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Balci, M., Krawiec, M., Ta§kesenligil, Y. et al. Structure of a ring enlarged product from the base induced rearrangement of dibromomethylenebenzonorbornene. J Chem Crystallogr 26, 413–418 (1996). https://doi.org/10.1007/BF01665821

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  • DOI: https://doi.org/10.1007/BF01665821

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