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Catalytic synthesis and transformations of magnesacycloalkanes

3. Cyclomagnesation of norbornenes catalyzed by Cp2ZrCl2

Abstract

Catalytic cyclometallation of bicyclo[2.2.1]hept-2-ene, spirocyclo[2.2.1]hept-2-ene-7.1'-cyclopropane andendo-tricyclo[5.2.1.02,6]deca-3,8-diene (dicyclopentadiene) with R2Mg (R =n-Pr,n-Bu) leading to the formation of polycyclic magnesacyclopentanes (MC) has been studied. The yield of MC and the selectivity of the reaction have been shown to depend on the ratio of starting reagents, the solvent, and temperature. The most probable scheme of the transformation studied is proposed.

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Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 165–169, January, 1993.

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Dzhemilev, U.M., Sultanov, R.M. & Gaimaldinov, R.G. Catalytic synthesis and transformations of magnesacycloalkanes. Russ Chem Bull 42, 149–153 (1993). https://doi.org/10.1007/BF00699998

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Key words

  • synthesis
  • catalysis
  • magnesacycloalkanes
  • norbornenes
  • cyclometallation
  • Zrcomplex
  • selectivity
  • mechanism
  • zirconacyclopentanes