Stereochemical study on the cycloaddition of a cyclic nitrone to 5‐methyl‐2(5H)‐furanone

Marta Figueredo, Josep Font, Pedro De March

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23 Citations (Scopus)

Abstract

The 1,3‐Dipolar cycloaddition of 3,4,5,6‐tetrahydropyridine 1‐oxide (1) to 5‐methyl‐2(5H)‐furanone (2) yields adducts 3, 4, and 5, whose stereochemistry has been established by a detailed study of their low‐temperature 1H‐NMR spectra. The major adduct, 4, arises from an exo transition state and an anti approach, indicating the dominance of steric factors over secondary orbital interactions. Copyright © 1989 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Original languageEnglish
Pages (from-to)1701-1704
JournalChemische Berichte
Volume122
Issue number9
DOIs
Publication statusPublished - 1 Jan 1989

Keywords

  • 1,3‐Dipolar cycloaddition
  • 3,4,5,6‐Tetrahydropyridine 1‐oxide
  • 5‐Methyl‐2(5H)‐furanone
  • Methyl sorbate

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