Arene oxidation with malonoyl peroxides

Andrei Dragan; Tomasz M. Kubczyk; Julian H. Rowley; Stephen Sproules; Nicholas C. O. Tomkinson

doi:10.1021/acs.orglett.5b00953

Arene oxidation with malonoyl peroxides

Andrei Dragan, Tomasz M. Kubczyk, Julian H. Rowley, Stephen Sproules, Nicholas C. O. Tomkinson^*

^*Corresponding author for this work

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

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Abstract

Malonoyl peroxide 7, prepared in a single step from the commercially available diacid, is an effective reagent for the oxidation of aromatics. Reaction of an arene with peroxide 7 at room temperature leads to the corresponding protected phenol which can be unmasked by aminolysis. An ionic mechanism consistent with the experimental findings and supported by isotopic labeling, Hammett analysis, EPR investigations, and reactivity profile studies is proposed.

Original language	English
Pages (from-to)	2618-2621
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	11
Early online date	12 May 2015
DOIs	https://doi.org/10.1021/acs.orglett.5b00953
Publication status	Published - 5 Jun 2015

Keywords

malonoyl peroxide 7
diacid
aminolysis

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Dragan-et-al-OL2015-arene-oxidation-with-malonoyl-peroxidesAccepted author manuscript, 1.65 MB

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title = "Arene oxidation with malonoyl peroxides",

abstract = "Malonoyl peroxide 7, prepared in a single step from the commercially available diacid, is an effective reagent for the oxidation of aromatics. Reaction of an arene with peroxide 7 at room temperature leads to the corresponding protected phenol which can be unmasked by aminolysis. An ionic mechanism consistent with the experimental findings and supported by isotopic labeling, Hammett analysis, EPR investigations, and reactivity profile studies is proposed.",

keywords = "malonoyl peroxide 7, diacid, aminolysis",

author = "Andrei Dragan and Kubczyk, {Tomasz M.} and Rowley, {Julian H.} and Stephen Sproules and Tomkinson, {Nicholas C. O.}",

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T1 - Arene oxidation with malonoyl peroxides

AU - Dragan, Andrei

AU - Kubczyk, Tomasz M.

AU - Rowley, Julian H.

AU - Sproules, Stephen

AU - Tomkinson, Nicholas C. O.

PY - 2015/6/5

Y1 - 2015/6/5

N2 - Malonoyl peroxide 7, prepared in a single step from the commercially available diacid, is an effective reagent for the oxidation of aromatics. Reaction of an arene with peroxide 7 at room temperature leads to the corresponding protected phenol which can be unmasked by aminolysis. An ionic mechanism consistent with the experimental findings and supported by isotopic labeling, Hammett analysis, EPR investigations, and reactivity profile studies is proposed.

AB - Malonoyl peroxide 7, prepared in a single step from the commercially available diacid, is an effective reagent for the oxidation of aromatics. Reaction of an arene with peroxide 7 at room temperature leads to the corresponding protected phenol which can be unmasked by aminolysis. An ionic mechanism consistent with the experimental findings and supported by isotopic labeling, Hammett analysis, EPR investigations, and reactivity profile studies is proposed.

KW - malonoyl peroxide 7

KW - diacid

KW - aminolysis

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UR - http://pubs.acs.org/journal/orlef7

U2 - 10.1021/acs.orglett.5b00953

DO - 10.1021/acs.orglett.5b00953

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VL - 17

SP - 2618

EP - 2621

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Arene oxidation with malonoyl peroxides

Abstract

Keywords

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