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Russian Journal of Organic Chemistry

, Volume 50, Issue 7, pp 1003–1005 | Cite as

Quantum chemical study of the products and hypothetical intermediates in the dehydrobromination of bromobullvalene in furan

  • S. G. Semenov
  • M. V. Makarova
Article

Abstract

Equilibrium structural parameters of didehydrobullvalene, its adducts with furan, and tris(didehydrobullvalene) and bullvalenophenol tautomers have been determined by DFT M06-2X/cc-pVTZ quantum chemical calculations. The energies of the assumed Diels-Alder adducts are considerably higher than the energies of the isolated products, and the energy barriers separating them are fairly low. Interconversion of enantiomers of the major adduct via two sequential Cope rearrangements with calculated barriers of 17.2 and 15.0 kcal/mol, respectively, may be regarded as an example of truly degenerate mediated tautomerism.

Keywords

Adduct Furan Quantum Chemical Study Alder Reaction Mutual Transformation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2014

Authors and Affiliations

  1. 1.St. Petersburg State UniversitySt. PetersburgRussia

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