Nitrogen oxides/selenium dioxide-mediated benzylic oxidations

Joseph E. Remias; Ayusman Sen

doi:10.1016/S1381-1169(03)00153-5

Nitrogen oxides/selenium dioxide-mediated benzylic oxidations

Joseph E. Remias, Ayusman Sen

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

7 Scopus citations

Abstract

The oxidation of benzylic groups to the corresponding carboxylic acid functionality by dioxygen is mediated by a combination of nitrogen oxides and selenium dioxide (SeO₂). Substrates examined include alkylnaphthalenes and alkylpyridines. The aldehyde appears to be an intermediate in the reaction. Mechanistic studies suggest that the rate-determining step is hydrogen atom abstraction by nitrogen dioxide (NO₂) to form the benzyl radical. Selenium dioxide subsequently oxidizes this radical to the desired product.

Original language	English (US)
Pages (from-to)	63-70
Number of pages	8
Journal	Journal of Molecular Catalysis A: Chemical
Volume	201
Issue number	1-2
DOIs	https://doi.org/10.1016/S1381-1169(03)00153-5
State	Published - Jul 1 2003

All Science Journal Classification (ASJC) codes

Catalysis
Process Chemistry and Technology
Physical and Theoretical Chemistry

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10.1016/S1381-1169(03)00153-5

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title = "Nitrogen oxides/selenium dioxide-mediated benzylic oxidations",

abstract = "The oxidation of benzylic groups to the corresponding carboxylic acid functionality by dioxygen is mediated by a combination of nitrogen oxides and selenium dioxide (SeO2). Substrates examined include alkylnaphthalenes and alkylpyridines. The aldehyde appears to be an intermediate in the reaction. Mechanistic studies suggest that the rate-determining step is hydrogen atom abstraction by nitrogen dioxide (NO2) to form the benzyl radical. Selenium dioxide subsequently oxidizes this radical to the desired product.",

author = "Remias, {Joseph E.} and Ayusman Sen",

note = "Funding Information: JER thanks the NCER STAR/EPA fellowship for financial support. This work was funded by Dow Chemical and the National Science Foundation.",

year = "2003",

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doi = "10.1016/S1381-1169(03)00153-5",

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T1 - Nitrogen oxides/selenium dioxide-mediated benzylic oxidations

AU - Remias, Joseph E.

AU - Sen, Ayusman

N1 - Funding Information: JER thanks the NCER STAR/EPA fellowship for financial support. This work was funded by Dow Chemical and the National Science Foundation.

PY - 2003/7/1

Y1 - 2003/7/1

N2 - The oxidation of benzylic groups to the corresponding carboxylic acid functionality by dioxygen is mediated by a combination of nitrogen oxides and selenium dioxide (SeO2). Substrates examined include alkylnaphthalenes and alkylpyridines. The aldehyde appears to be an intermediate in the reaction. Mechanistic studies suggest that the rate-determining step is hydrogen atom abstraction by nitrogen dioxide (NO2) to form the benzyl radical. Selenium dioxide subsequently oxidizes this radical to the desired product.

AB - The oxidation of benzylic groups to the corresponding carboxylic acid functionality by dioxygen is mediated by a combination of nitrogen oxides and selenium dioxide (SeO2). Substrates examined include alkylnaphthalenes and alkylpyridines. The aldehyde appears to be an intermediate in the reaction. Mechanistic studies suggest that the rate-determining step is hydrogen atom abstraction by nitrogen dioxide (NO2) to form the benzyl radical. Selenium dioxide subsequently oxidizes this radical to the desired product.

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U2 - 10.1016/S1381-1169(03)00153-5

DO - 10.1016/S1381-1169(03)00153-5

M3 - Article

AN - SCOPUS:0038172308

SN - 1381-1169

VL - 201

SP - 63

EP - 70

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

IS - 1-2

ER -

Nitrogen oxides/selenium dioxide-mediated benzylic oxidations

Abstract

All Science Journal Classification (ASJC) codes

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