4+3 Cycloaddition reactions of halogen-substituted cyclohexenyl oxyallylic cations

Michael Harmata, Lixin Shao, Laszlo Kürti, Asitha Abeywardane

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

2,6-Dibromo- and 2,2-dichlorocyclohexanone react with base in the presence of various dienes to give 4+3 cycloadducts in fair to good yields. Preliminary studies of the cycloadducts suggest that they are unstable and are recalcitrant to nucleophilic addition and cross-metathesis. However, the LAH reduction products undergo a quasi-Favorskii rearrangement upon treatment with potassium hydride and one cycloadduct derivative was dehalogenated using radical chemistry.

Original languageEnglish (US)
Pages (from-to)1075-1078
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number6
DOIs
StatePublished - Feb 5 1999

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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