Expected and unexpected products from reacting Sanger’s reagent with                        p-phenylenediamine

Michael Plater; William Harrison

doi:10.1177/17475198231212673

Expected and unexpected products from reacting Sanger’s reagent with p-phenylenediamine

Michael Plater^* (Corresponding Author), William Harrison

^*Corresponding author for this work

Chemistry

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

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Abstract

p-Phenylenediamine reacts with Sanger’s reagent in hot ethanol to give the expected monoand di-substitution products, but in ethanol at rt it gave exclusively 2-nitro-5-fluorophenyl-pphenylenediamine where a hydrogen atom is displaced by attack at an activated, unsubstituted position. The reactions of p-phenylenediamine and aniline with Sangers reagent were compared in the cheap, ‘green’ solvent ethanol.

Original language	English
Journal	Journal of Chemical Research
Volume	47
Issue number	6
Early online date	28 Nov 2023
DOIs	https://doi.org/10.1177/17475198231212673
Publication status	Published - Dec 2023

Bibliographical note

Acknowledgments
We thank the UK EPSRC National Mass Spectrometry Service Centre for mass spectrometric data and the UK National Crystallography Centre (University of Southampton) for the X-ray data collections. M.J.P. performed all synthesis and obtained the characterisation data and WTA Harrison solved the crystallographic data sets. Data sets were obtained free of charge from the National Crystallography Centre, University of Southampton.

Funding
The author(s) received no financial support for the research, authorship and/or publication of this article.

Keywords

2,4-Dinitrofluorobenzene
Sanger’s reagent
p-phenylenediamine
aniline
glycine

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10.1177/17475198231212673

Plater_Etal_JCR_Expected_And_Unexpected_VOR
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Cite this

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title = "Expected and unexpected products from reacting Sanger{\textquoteright}s reagent with p-phenylenediamine",

abstract = "p-Phenylenediamine reacts with Sanger{\textquoteright}s reagent in hot ethanol to give the expected monoand di-substitution products, but in ethanol at rt it gave exclusively 2-nitro-5-fluorophenyl-pphenylenediamine where a hydrogen atom is displaced by attack at an activated, unsubstituted position. The reactions of p-phenylenediamine and aniline with Sangers reagent were compared in the cheap, {\textquoteleft}green{\textquoteright} solvent ethanol.",

keywords = "2,4-Dinitrofluorobenzene, Sanger{\textquoteright}s reagent, p-phenylenediamine, aniline, glycine",

author = "Michael Plater and William Harrison",

note = "Acknowledgments We thank the UK EPSRC National Mass Spectrometry Service Centre for mass spectrometric data and the UK National Crystallography Centre (University of Southampton) for the X-ray data collections. M.J.P. performed all synthesis and obtained the characterisation data and WTA Harrison solved the crystallographic data sets. Data sets were obtained free of charge from the National Crystallography Centre, University of Southampton. Funding The author(s) received no financial support for the research, authorship and/or publication of this article.",

year = "2023",

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doi = "10.1177/17475198231212673",

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journal = "Journal of Chemical Research",

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AU - Plater, Michael

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N1 - Acknowledgments We thank the UK EPSRC National Mass Spectrometry Service Centre for mass spectrometric data and the UK National Crystallography Centre (University of Southampton) for the X-ray data collections. M.J.P. performed all synthesis and obtained the characterisation data and WTA Harrison solved the crystallographic data sets. Data sets were obtained free of charge from the National Crystallography Centre, University of Southampton. Funding The author(s) received no financial support for the research, authorship and/or publication of this article.

PY - 2023/12

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N2 - p-Phenylenediamine reacts with Sanger’s reagent in hot ethanol to give the expected monoand di-substitution products, but in ethanol at rt it gave exclusively 2-nitro-5-fluorophenyl-pphenylenediamine where a hydrogen atom is displaced by attack at an activated, unsubstituted position. The reactions of p-phenylenediamine and aniline with Sangers reagent were compared in the cheap, ‘green’ solvent ethanol.

AB - p-Phenylenediamine reacts with Sanger’s reagent in hot ethanol to give the expected monoand di-substitution products, but in ethanol at rt it gave exclusively 2-nitro-5-fluorophenyl-pphenylenediamine where a hydrogen atom is displaced by attack at an activated, unsubstituted position. The reactions of p-phenylenediamine and aniline with Sangers reagent were compared in the cheap, ‘green’ solvent ethanol.

KW - 2,4-Dinitrofluorobenzene

KW - Sanger’s reagent

KW - p-phenylenediamine

KW - aniline

KW - glycine

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