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Issue 46, 2013
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A simple and rapid route to novel tetra(4-thiaalkyl)ammonium bromides

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Abstract

A simple approach for the preparation of symmetrical quaternary ammonium bromides employing thiol–ene click chemistry is used to synthesize tetra(4-thiaalkyl)ammonium bromides. This approach allows the incorporation of a variety of alkyl moieties onto the nitrogen center with a one-step synthesis involving easy work-up, no side reactions and environmentally friendly reagents. To elucidate information regarding the behaviour of this novel class of compounds, comparisons to tetraalkylammonium analogues have been made. These include melting points, activity as phase-transfer catalysts, and conformational predictions from computational modelling. All results are consistent in indicating stronger bonding between the quaternary cation and the anion for the salts with 4-thiaalkyl chains as compared to those with n-alkyl chains.

Graphical abstract: A simple and rapid route to novel tetra(4-thiaalkyl)ammonium bromides

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Submitted
31 Jul 2013
Accepted
07 Oct 2013
First published
14 Oct 2013

RSC Adv., 2013,3, 24612-24617
Article type
Paper

A simple and rapid route to novel tetra(4-thiaalkyl)ammonium bromides

R. A. O'Brien, C. W. West, B. E. Hollingsworth, A. C. Stenson, C. B. Henderson, A. Mirjafari, N. Mobarrez, K. N. West, K. M. Mattson, E. A. Salter, A. Wierzbicki and J. H. Davis, RSC Adv., 2013, 3, 24612
DOI: 10.1039/C3RA44042G

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