Chiral Thianthrenes

Michael Plater; William TA  Harrison

doi:10.3390/ijms25084311

Chiral Thianthrenes

Michael Plater^* (Corresponding Author), William TA Harrison

^*Corresponding author for this work

Chemistry

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

Abstract

The absolute configuration and stability of two thianthrene chiral sulfoxides has been determined by means of X-ray single-crystal structure determinations. The analyses and configurations allow verification that the diastereomeric sulfoxides are stable in solution and are not interconverting, which has been suggested in some studies of sulfoxides. The two thianthrene sulfoxides have slightly different Rf values, which allowed their separation using flash chromatography on silica. The spots run back-to-back, which posed a challenge for their separation. The pure, separated compounds in solution remain as separate, single spots on a Thin Layer Chromatography (TLC) plate.

Original language	English
Article number	4311
Number of pages	9
Journal	Physical Chemistry Chemical Physics
Volume	25
Issue number	8
Early online date	13 Apr 2024
DOIs	https://doi.org/10.3390/ijms25084311
Publication status	Published - 13 Apr 2024

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. Plater performed all syntheses and obtained the characterisation data, and W. T. A. Harrison solved the crystallographic data sets. Data sets were obtained free of charge from the National Crystallography Centre, Southampton University.

Data Availability Statement

CCDC-2337820 and CCDC-2337821 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge by emailing hello@ccdc.cam.ac.uk or by contacting The Cambridge Crystallography Centre, 12 Union Road, Cambridge, CB2 1EZ, UK;
https://www.ccdc.cam.ac.uk/ (accessed on 5 March 2024).

Keywords

thianthrene
dithiin
sulfoxide
chiral sulfoxide
configuration
diastereoisomer
Resolution

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Plater_etal_IJMS_CHiral_Thianthrees_VoR
© 2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
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Data From Chiral Thianthrenes
Plater, M. J. (Creator) & Harrison, W. (Creator), University of Aberdeen, 13 Apr 2024
DOI: 10.3390/ijms25084311, https://www.mdpi.com/article/10.3390/ijms25084311/s1
Dataset

Cite this

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N2 - The absolute configuration and stability of two thianthrene chiral sulfoxides has been determined by means of X-ray single-crystal structure determinations. The analyses and configurations allow verification that the diastereomeric sulfoxides are stable in solution and are not interconverting, which has been suggested in some studies of sulfoxides. The two thianthrene sulfoxides have slightly different Rf values, which allowed their separation using flash chromatography on silica. The spots run back-to-back, which posed a challenge for their separation. The pure, separated compounds in solution remain as separate, single spots on a Thin Layer Chromatography (TLC) plate.

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KW - dithiin

KW - sulfoxide

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KW - configuration

KW - diastereoisomer

KW - Resolution

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ER -

Chiral Thianthrenes

Abstract

Bibliographical note

Data Availability Statement

Keywords

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Datasets

Data From Chiral Thianthrenes

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