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

Ken S. Feldman

doi:10.1021/jo9704220

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

Ken S. Feldman

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	4983-4990
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	62
Issue number	15
DOIs	https://doi.org/10.1021/jo9704220
State	Published - Jul 25 1997

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo9704220

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title = "Cyclization pathways of a (Z)-stilbene-derived bis(orthoquinone monoketal)",

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.",

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N2 - 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.

AB - 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.

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ER -

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

Abstract

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