Iron(II)-promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes: A mechanism distinct from that postulated previously

Masaki Kamata, Chika Satoh, Hye-Sook Kim, Yusuke Wataya

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Reactions of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes 1a-c (1a: Ar=p-FC6H4, 1b: Ar=C6H5, 1c: Ar=p-MeC6H4) with FeBr2 afforded syn-1,2;3,4-bis(epoxy)-1,4-diarylcyclohexanes 4a-c and cis-3,6-diaryl-2,3-epoxycyclohexanones 5a-c as major products instead of the previously reported 1-aroyl-3-aryl-2,3-epoxycyclopentanes 2a-c.

Original languageEnglish
Pages (from-to)8313-8317
Number of pages5
JournalTetrahedron Letters
Volume43
Issue number46
DOIs
Publication statusPublished - Nov 11 2002

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Keywords

  • 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-ene
  • Antimalarial cyclic peroxide
  • Bicyclic peroxide
  • Diepoxide
  • Epoxyketone
  • FeBr
  • Malaria
  • Mechanism
  • Rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Iron(II)-promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes : A mechanism distinct from that postulated previously. / Kamata, Masaki; Satoh, Chika; Kim, Hye-Sook; Wataya, Yusuke.

In: Tetrahedron Letters, Vol. 43, No. 46, 11.11.2002, p. 8313-8317.

Research output: Contribution to journalArticle

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abstract = "Reactions of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes 1a-c (1a: Ar=p-FC6H4, 1b: Ar=C6H5, 1c: Ar=p-MeC6H4) with FeBr2 afforded syn-1,2;3,4-bis(epoxy)-1,4-diarylcyclohexanes 4a-c and cis-3,6-diaryl-2,3-epoxycyclohexanones 5a-c as major products instead of the previously reported 1-aroyl-3-aryl-2,3-epoxycyclopentanes 2a-c.",
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