ON THE PRINS REACTION OF TERMINAL OLEFINS AND FORMALDEHYDE IN TRIFLUOROACETIC ACID

Authors

  • Hasanain A. A. Almohseni Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA
  • Matthew A. H. Stent Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA
  • David M. Hodgson Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA

DOI:

https://doi.org/10.1007/4363

Keywords:

formaldehyde, terminal alkenes, tetrahydropyrans, trifluoroacetic acid, Prins reaction

Abstract

The Prins reaction of 1-heptene, as a representative terminal alkene, with formaldehyde in trifluoroacetic acid produces 3-butyl-4-(trifluoroacetoxy)tetrahydropyran and/or 3-butyl-4-hydroxytetrahydropyran; it does not provide (as previously reported by Talipov and coworkers) a route to 3-alkyl-2,5-dihydrofurans and 4-alkyl-3-hydroxytetrahydrofurans.

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Published

2018-06-05

Issue

Vol. 54 No. 4 (2018): Stereoselective synthesis of heterocyclic compounds

Section

Short Communications