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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
  • 35 Downloads

Conclusions

  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.

     

Keywords

Formaldehyde Hydrochloric Acid Octane Cyclopentene Prins Reaction 
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

© 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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