Cyclization pathways of a (Z)-stilbene-derived bis(orthoquinone monoketal)

Ken S. Feldman

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20 Scopus citations

Abstract

Lead tetraacetate mediated oxidation of a (Z)-bisphenolic stilbene derivative affords a bis(orthoquinone monoketal) product. Thermolysis studies of this highly unsaturated dione reveal that sigmatropic hydrogen shifts, followed by either of two distinct solvolytic ring closures, constitute the predominate reaction pathways under heating. No evidence for a desired 6π electron electrocyclization was forthcoming.

Original languageEnglish (US)
Pages (from-to)4983-4990
Number of pages8
JournalJournal of Organic Chemistry
Volume62
Issue number15
DOIs
StatePublished - Jul 25 1997

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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