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Russian Journal of Organic Chemistry

, Volume 44, Issue 1, pp 62–66 | Cite as

Tandem molecular rearrangement in the alkylation of phenol with camphene

  • I. Yu. Chukicheva
  • L. V. Spirikhin
  • A. V. Kuchin
Article

Abstract

The alkylation of phenol with camphene in the presence of boron trifluoride in glacial acetic acid was accompanied by tandem molecular rearrangement with formation of a mixture of ortho- and para-substituted phenols having 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl and 5,5,6-trimethylbicyclo[2.2.1]hept-exo-2-yl substituents. The same products were obtained by rearrangement of 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yloxybenzene under analogous conditions. Similar reactions performed in the presence of aluminum phenoxide as catalyst resulted in predominant formation of the corresponding ortho-substituted phenols.

Keywords

Alkylation Camphene Boron Trifluoride Terpene Fragment Aluminum Phenoxide 
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. 2008

Authors and Affiliations

  • I. Yu. Chukicheva
    • 1
  • L. V. Spirikhin
    • 2
  • A. V. Kuchin
    • 1
  1. 1.Institute of Chemistry, Komi Research Center, Ural DivisionRussian Academy of SciencesSyktyvkarRussia
  2. 2.Institute of Organic Chemistry, Ufa Research CenterRussian Academy of SciencesUfaRussia

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