A study of mono-, di- and tri-tosylated amines: An unexpected sulfonamide

John Plater; William T. A. Harrison

doi:10.1177/17475198231194866

A study of mono-, di- and tri-tosylated amines: An unexpected sulfonamide

John Plater^* (Corresponding Author), William T. A. Harrison

^*Corresponding author for this work

Chemistry

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

Abstract

2-Aminobenzylaniline was ditosylated and gave an unexpected product N,N-ditosylamino-2-benzylaminobenzene in which the primary amine had ditosylated, and the benzylamine was unreacted. The benzylamine, although more electron rich, is sterically crowded and less nucleophilic than the primary amine in this ditosylated system. Sterically crowded tosylamides were prepared by reacting o-phenylenediamine, p-phenylenediamine and 1,8-diaminonaphthalene with tosyl chloride.

Original language	English
Pages (from-to)	1-7
Number of pages	1
Journal	Journal of Chemical Research
Volume	47
Issue number	4
Early online date	18 Aug 2023
DOIs	https://doi.org/10.1177/17475198231194866
Publication status	Published - 18 Aug 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.
Funding
The author(s) received no financial support for the research, authorship, and/or publication of this article.

Keywords

crystal structure
o-phenylenediamines
sulfonamide
tosylamide
tosylchloride

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Cite this

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title = "A study of mono-, di- and tri-tosylated amines: An unexpected sulfonamide",

abstract = "2-Aminobenzylaniline was ditosylated and gave an unexpected product N,N-ditosylamino-2-benzylaminobenzene in which the primary amine had ditosylated, and the benzylamine was unreacted. The benzylamine, although more electron rich, is sterically crowded and less nucleophilic than the primary amine in this ditosylated system. Sterically crowded tosylamides were prepared by reacting o-phenylenediamine, p-phenylenediamine and 1,8-diaminonaphthalene with tosyl chloride.",

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

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N2 - 2-Aminobenzylaniline was ditosylated and gave an unexpected product N,N-ditosylamino-2-benzylaminobenzene in which the primary amine had ditosylated, and the benzylamine was unreacted. The benzylamine, although more electron rich, is sterically crowded and less nucleophilic than the primary amine in this ditosylated system. Sterically crowded tosylamides were prepared by reacting o-phenylenediamine, p-phenylenediamine and 1,8-diaminonaphthalene with tosyl chloride.

AB - 2-Aminobenzylaniline was ditosylated and gave an unexpected product N,N-ditosylamino-2-benzylaminobenzene in which the primary amine had ditosylated, and the benzylamine was unreacted. The benzylamine, although more electron rich, is sterically crowded and less nucleophilic than the primary amine in this ditosylated system. Sterically crowded tosylamides were prepared by reacting o-phenylenediamine, p-phenylenediamine and 1,8-diaminonaphthalene with tosyl chloride.

KW - crystal structure

KW - o-phenylenediamines

KW - sulfonamide

KW - tosylamide

KW - tosylchloride

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DO - 10.1177/17475198231194866

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SP - 1

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JO - Journal of Chemical Research

JF - Journal of Chemical Research

IS - 4

ER -

A study of mono-, di- and tri-tosylated amines: An unexpected sulfonamide

Abstract

Bibliographical note

Keywords

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