Prins reaction with cyclopentene and synthesis of hydroxymethyl-2-cyclopentene

  • N. P. Volynskii
  • G. D. Gal'pern
  • N. G. Shishkovskaya
  • A. Yu. Koshevnik
  • L. R. Barykina
Organic and Biological Chemistry


  1. 1.

    The reaction of cyclopentene, formaldehyde and hydrochloric acid gives a mixture of the cis-and trans-4, 5-trimethylene-1, 3-dioxanes (0.8%) in a 2∶1 ratio, trans-6-chloro-cis-3-oxabicyclo[3.3.0]octane (5.5%), trans-8-chloro-cis-3-oxabicyclo[3.2.1]-octane (5.5%), and the cis- and trans-1-hydroxymethy1-2-chlorocyclopentanes (or their formals) in a 1∶9 ratio.

  2. 2.

    The dehydrochlorination of the mixed 1-hydroxymethy1-2-chlorocyclopentane formals and subsequent methanolysis lead to the formation of the hydroxymethy1-1- and -2-cyclopentenes in a 1∶9 ratio.

  3. 3.

    The Prins reaction with cyclopentene proceeds nonstereospecifically, which is explained by the formation of the free carbcation in the first step.



Formaldehyde Hydrochloric Acid Octane Cyclopentene Prins Reaction 
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Copyright information

© Consultants Bureau 1973

Authors and Affiliations

  • N. P. Volynskii
    • 1
  • G. D. Gal'pern
    • 1
  • N. G. Shishkovskaya
    • 1
  • A. Yu. Koshevnik
    • 1
  • L. R. Barykina
    • 1
  1. 1.A. V. Topchiev Institute of Petrochemical SynthesisAcademy of Sciences of the USSRUSSR

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