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Arene oxidation with malonoyl peroxides.

Andrei Dragan1, Tomasz M Kubczyk1, Julian H Rowley1

  • 1†WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, U.K.

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Summary
This summary is machine-generated.

Malonoyl peroxide 7 oxidizes aromatic compounds to protected phenols. This novel reagent offers an efficient, single-step synthesis and a proposed ionic mechanism for aromatic oxidation.

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Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms

Background:

  • Aromatic compounds are fundamental building blocks in organic chemistry.
  • Efficient oxidation methods are crucial for synthesizing functionalized aromatic derivatives.

Purpose of the Study:

  • To introduce malonoyl peroxide 7 as a novel reagent for aromatic oxidation.
  • To elucidate the reaction mechanism of this oxidation process.

Main Methods:

  • Single-step preparation of malonoyl peroxide 7 from a commercially available diacid.
  • Room temperature reaction of arenes with malonoyl peroxide 7.
  • Unmasking of protected phenols via aminolysis.
  • Mechanistic studies including isotopic labeling, Hammett analysis, EPR, and reactivity profiling.

Main Results:

  • Malonoyl peroxide 7 effectively oxidizes aromatic compounds to protected phenols.
  • The reaction proceeds efficiently at room temperature.
  • An ionic mechanism was proposed and supported by experimental evidence.

Conclusions:

  • Malonoyl peroxide 7 is a potent and versatile reagent for the oxidation of aromatic systems.
  • The proposed ionic mechanism provides insight into the reactivity of malonoyl peroxide 7.
  • This method offers a convenient route to protected phenols from readily available starting materials.