The reaction of enols with superoxide anion radical [02???]1. Synthesis of 2,3-unsaturated-δ-valerolactones.

Aryeh A. Frimer, Pessia Gilinsky-Sharon, Gladis Aljadeff

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Abstract

3- and 4-Hydroxycoumarin (1 and 3) as well as 2-hydroxy-2,5-cyclohexadien-1-ones 5a-f were reacted with KO2/18-crown-6 in benzene. Initial deprotonation of the enol hydrogen was followed by nucleophilic attack by O2{radical dot}/t- (for 1 and 3) and/or autoxidation of the resulting anion (for 1 and 5a-e). A convenient synthesis of 2,3-unsaturated-δ-valerolactones from the corresponding 2-cyclohexen-1-ones is also described.

Original languageEnglish
Pages (from-to)1301-1304
Number of pages4
JournalTetrahedron Letters
Volume23
Issue number12
DOIs
StatePublished - 1982

Bibliographical note

Funding Information:
16. We acknowledge the support of the Israel National Council for Research and Development.

Funding

16. We acknowledge the support of the Israel National Council for Research and Development.

FundersFunder number
Israel National Council for Research and Development

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