Reaction of superoxide with alkyl halides and tosylates

San Filippo, Joseph; Chern, Chuen-Ing; Valentine, Joan S.

doi:10.1021/jo00899a048

Cited by 105Oxidative Organic Chemistry ReactionsChemical Synthesis and ReactionsPhysical Organic Chemistry and Reaction Kinetics

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Reaction of superoxide with alkyl halides and tosylates

San Filippo, Joseph, Chern, Chuen-Ing, Valentine, Joan S.·1975·The Journal of Organic Chemistry

DOI 10.1021/jo00899a048

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ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTReaction of superoxide with alkyl halides and tosylatesJoseph San Filippo Jr., Chuen-Ing Chern, and Joan S. ValentineCite this: J. Org. Chem. 1975, 40, 11, 1678–1680Publication Date (Print):May 1, 1975Publication History Published online1 May 2002Published inissue 1 May 1975https://pubs.acs.org/doi/10.1021/jo00899a048https://doi.org/10.1021/jo00899a048research-articleACS PublicationsRequest reuse permissionsArticle Views644Altmetric-Citations90LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

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The structure of the alkyl group, the leaving group, and solvent polarity influence the carbon-oxygen bond formation step in a way consistent with an SN2 displacement on carbon.
“Furthermore, it has been observed that the structure of the alkyl group attached to the halogen, the nature of the leaving group, and the polarity of the solvent exert influence on the course of the reaction in the carbon–oxygen bond formation step that is consistent with a mechanism involving an SN2 displacement on the carbon; therefore, it follows that the initial reaction of the superoxide with”
From Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity (2023) · cites this paper as [130]
The initial reaction of superoxide with an alkyl halide produces an alkylperoxy radical.
“therefore, it follows that the initial reaction of the superoxide with an alkyl halide produces an alkylperoxy radical [130], Figure 48.”
From Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity (2023) · cites this paper as [130]

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A study of superoxide reactivity. Reaction of potassium superoxide with alkyl halides and tosylates
Chern, C.-I., DiCosimo, R., De Jesus, R., & San Filippo, J. (1978) · Journal of the American Chemical Society · doi:10.1021/ja00491a032 · Cited by 43
Self-citation
Superoxide chemistry. Reactions of superoxide with alkyl halides and alkyl sulfonate esters
Johnson, R. A., Nidy, E. G., & Merritt, M. V. (1978) · Journal of the American Chemical Society · doi:10.1021/ja00493a028 · Cited by 49
Electrochemical studies of the reactivity of superoxide ion with several alkyl halides in dimethyl sulfoxide
Merritt, M. V., & Sawyer, D. T. (1970) · The Journal of Organic Chemistry · doi:10.1021/jo00832a011 · Cited by 94
Reaction of tert-butyl hydroperoxide anion with dimethyl sulfoxide. On the pathway of the superoxide-alkyl halide reaction
Gibian, M. J., & Ungermann, T. (1976) · The Journal of Organic Chemistry · doi:10.1021/jo00876a037 · Cited by 36
Cooxidation reactions during oxidations of superoxide with polyhalides, carbon dioxide, phosphates, and acyl halides
Nagano, T., Yamamoto, H., & Hirobe, M. (1990) · Journal of the American Chemical Society · doi:10.1021/ja00165a042 · Cited by 22

Authors: San Filippo, J., Chern, C.-I., & Valentine, J. S.
ORCID: Valentine, Joan S.
Venue: The Journal of Organic Chemistry
Publisher: American Chemical Society (ACS)
Published: 1975-05
Volume: 40
Issue: 11
Pages: 1678-1680
ISSN: 0022-3263 (ISSN-L)
1520-6904
DOI: 10.1021/jo00899a048
OpenAlex: W2952115195
Cited by: 105
References: 0
Citations by year: 2026: 1 · 2025: 2 · 2024: 1 · 2023: 1 · 2022: 1 · 2020: 1 · 2019: 2 · 2017: 2 · 2016: 2 · 2015: 1 · 2014: 2 · 2012: 1
FWCI: 12.06
Type: journal article
Language: en
Open access: closed
Locations: The Journal of Organic Chemistry (publishedVersion)
Topics: Physical Sciences › Chemistry › Organic Chemistry › Oxidative Organic Chemistry Reactions
Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Reactions
Physical Sciences › Chemistry › Organic Chemistry › Physical Organic Chemistry and Reaction Kinetics
Keywords: superoxide, alkyl halides, tosylate, radical reactions, alkyl radicals, radical cations

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Reaction of superoxide with alkyl halides and tosylates

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