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

doi:10.1016/s0040-4039(00)87089-6

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

Department of Chemistry

Bar-Ilan University

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

18 Scopus citations

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 language	English
Pages (from-to)	1301-1304
Number of pages	4
Journal	Tetrahedron Letters
Volume	23
Issue number	12
DOIs	https://doi.org/10.1016/s0040-4039(00)87089-6
State	Published - 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.

Funders	Funder number
Israel National Council for Research and Development

Access to Document

10.1016/s0040-4039(00)87089-6

Cite this

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

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.",

author = "Frimer, {Aryeh A.} and Pessia Gilinsky-Sharon and Gladis Aljadeff",

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journal = "Tetrahedron Letters",

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T1 - The reaction of enols with superoxide anion radical [02???]1. Synthesis of 2,3-unsaturated-δ-valerolactones.

AU - Frimer, Aryeh A.

AU - Gilinsky-Sharon, Pessia

AU - Aljadeff, Gladis

N1 - Funding Information: 16. We acknowledge the support of the Israel National Council for Research and Development.

PY - 1982

Y1 - 1982

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AB - 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.

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