title: Unusual hydroxyl effect on fulvene endoperoxide decompositions.
abstract: The thermal decomposition of fulvene endoperoxides ordinarily proceeds via an allene oxide intermediate affording oxepin-2(3H)-one derivatives. We have now uncovered new, unusual pathways in these decompositions where the presence of a hydroxyl group on the alkyl or aryl attached to the fulvene exocyclic double bond has a profound effect on the fate of the reactive intermediates derived from the unstable endoperoxides. Computational work supports the proposed mechanistic pathways.
authors.affiliation: San Francisco State University, Department of Chemistry and Biochemistry, 1600 Holloway Avenue, San Francisco, CA 94132, USA.
authors.forename: Ihsan
authors.initials: I
authors.lastname: Erden
authors.affiliation: San Francisco State University, Department of Chemistry and Biochemistry, 1600 Holloway Avenue, San Francisco, CA 94132, USA.
authors.forename: John
authors.initials: J
authors.lastname: Basada
authors.affiliation: San Francisco State University, Department of Chemistry and Biochemistry, 1600 Holloway Avenue, San Francisco, CA 94132, USA.
authors.forename: Daniela
authors.initials: D
authors.lastname: Poli
authors.affiliation: San Francisco State University, Department of Chemistry and Biochemistry, 1600 Holloway Avenue, San Francisco, CA 94132, USA.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Cabrera
authors.affiliation: San Francisco State University, Department of Chemistry and Biochemistry, 1600 Holloway Avenue, San Francisco, CA 94132, USA.
authors.forename: Fupei
authors.initials: F
authors.lastname: Xu
authors.affiliation: Department of Chemistry, Virginia Commonwealth University, 1001 West Main Street, Richmond, Virginia 23284, USA.
authors.forename: Scott
authors.initials: S
authors.lastname: Gronert
keywords: allene oxides; cyclopropanones; endoperoxides; fulvenes; oxy-allyl