Rhenium-catalyzed oxidation of arenes - An improved synthesis of vitamin K3

Wolfgang A. Herrmann; Joachim J. Haider; Richard W. Fischer

doi:10.1016/S1381-1169(98)00133-2

Rhenium-catalyzed oxidation of arenes - An improved synthesis of vitamin K₃

Wolfgang A. Herrmann, Joachim J. Haider, Richard W. Fischer

Technical University of Munich

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

56 Scopus citations

Abstract

2-Methylnaphthalene 1 is oxidized to 2-methyl-1,4-naphthoquinone 2 by virtue of a new catalyst system in high yields and selectivity. A mixture of aqueous hydrogen peroxide and acetic anhydride is used as oxidant in the presence of methyltrioxorhenium(VII) dissolved in acetic acid as solvent. The concentration of acetic acid in the reaction mixture plays a crucial role for the activation of acetic anhydride mediated by methyltrioxorhenium(VII).

Original language	English
Pages (from-to)	115-121
Number of pages	7
Journal	Journal of Molecular Catalysis A: Chemical
Volume	138
Issue number	2-3
DOIs	https://doi.org/10.1016/S1381-1169(98)00133-2
State	Published - 5 Feb 1999

Keywords

Acetic anhydride
Arene oxidation
Hydrogen peroxide
Methyltrioxorhenium
Vitamin K

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10.1016/S1381-1169(98)00133-2

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title = "Rhenium-catalyzed oxidation of arenes - An improved synthesis of vitamin K3",

abstract = "2-Methylnaphthalene 1 is oxidized to 2-methyl-1,4-naphthoquinone 2 by virtue of a new catalyst system in high yields and selectivity. A mixture of aqueous hydrogen peroxide and acetic anhydride is used as oxidant in the presence of methyltrioxorhenium(VII) dissolved in acetic acid as solvent. The concentration of acetic acid in the reaction mixture plays a crucial role for the activation of acetic anhydride mediated by methyltrioxorhenium(VII).",

keywords = "Acetic anhydride, Arene oxidation, Hydrogen peroxide, Methyltrioxorhenium, Vitamin K",

author = "Herrmann, {Wolfgang A.} and Haider, {Joachim J.} and Fischer, {Richard W.}",

note = "Funding Information: This research was financially supported by the Bayerische Forschungsverbund f{\"u}r Katalyse (FORKAT). Useful discussions with Dr. W. R. Thiel are gratefully acknowledged.",

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T1 - Rhenium-catalyzed oxidation of arenes - An improved synthesis of vitamin K3

AU - Herrmann, Wolfgang A.

AU - Haider, Joachim J.

AU - Fischer, Richard W.

N1 - Funding Information: This research was financially supported by the Bayerische Forschungsverbund für Katalyse (FORKAT). Useful discussions with Dr. W. R. Thiel are gratefully acknowledged.

PY - 1999/2/5

Y1 - 1999/2/5

N2 - 2-Methylnaphthalene 1 is oxidized to 2-methyl-1,4-naphthoquinone 2 by virtue of a new catalyst system in high yields and selectivity. A mixture of aqueous hydrogen peroxide and acetic anhydride is used as oxidant in the presence of methyltrioxorhenium(VII) dissolved in acetic acid as solvent. The concentration of acetic acid in the reaction mixture plays a crucial role for the activation of acetic anhydride mediated by methyltrioxorhenium(VII).

AB - 2-Methylnaphthalene 1 is oxidized to 2-methyl-1,4-naphthoquinone 2 by virtue of a new catalyst system in high yields and selectivity. A mixture of aqueous hydrogen peroxide and acetic anhydride is used as oxidant in the presence of methyltrioxorhenium(VII) dissolved in acetic acid as solvent. The concentration of acetic acid in the reaction mixture plays a crucial role for the activation of acetic anhydride mediated by methyltrioxorhenium(VII).

KW - Acetic anhydride

KW - Arene oxidation

KW - Hydrogen peroxide

KW - Methyltrioxorhenium

KW - Vitamin K

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U2 - 10.1016/S1381-1169(98)00133-2

DO - 10.1016/S1381-1169(98)00133-2

M3 - Article

AN - SCOPUS:0033524787

SN - 1381-1169

VL - 138

SP - 115

EP - 121

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

IS - 2-3

ER -

Rhenium-catalyzed oxidation of arenes - An improved synthesis of vitamin K₃

Abstract

Keywords

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