Synthesis of 3-(1-hydroxyalkyl)-5H-furan-2-ones: Study of their reaction with halogens

Angel Calderón, Pedro de March, Mustafa el Arrad, Josep Font

Research output: Contribution to journalArticleResearchpeer-review

10 Citations (Scopus)

Abstract

The synthesis of 3-(1-hydroxyalkyl)-5H-furan-2-ones; 4a-c, is reported. The reaction of lactones 4a and 4b with bromine under typical ionic bromination conditions gives as major product the unexpected substitution of the allylic hydroxyl group. Only the less hindered double bond in 4c gives some proportion of the normal addition product. The bromine chloride addition to 4c proceeds with 55% yield, while lactone 4a does not add BrCl. All these results point to the fact that halogen addition to the double bond of 4 suffers at least from steric hindrance. © 1994.
Original languageEnglish
Pages (from-to)4201-4214
JournalTetrahedron
Volume50
Issue number14
DOIs
Publication statusPublished - 4 Apr 1994

Keywords

  • 3-(1-hydroxyalkyl)-5H-furan-2-ones
  • bromination
  • bromine chlorination

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