Abstract
Vibration ball-milling in a zirconia-lined vessel afforded clean and quantitative nucleophilic displacement reactions between 4-methoxybenzylthiolate salts and nucleoside 5′-halides or 5′-tosylates in five to 60 minutes. Under these conditions, commonly-encountered nucleoside cyclisation byproducts (especially of purine nucleosides) were not observed. Liquid-assisted grinding of the same 5'-iodide and 5′-tosylate substrates with potassium selenocyanate in the presence of DMF produced the corresponding 5′-selenocyanates in variable yields over the course of between one and eleven hours thereby avoiding the preparation and use of hygroscopic tetrabutylammonium salts.
Original language | English |
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Pages (from-to) | 87–92 |
Number of pages | 6 |
Journal | Beilstein Journal of Organic Chemistry |
Volume | 13 |
DOIs | |
Publication status | Published - 13 Jan 2017 |
Keywords
- ball mill
- chalcogen
- mechanochemistry
- ; nucleophilic substitution
- nucleoside
ASJC Scopus subject areas
- Organic Chemistry
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Dive into the research topics of 'Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill'. Together they form a unique fingerprint.Student Theses
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Novel approaches to the synthesis of selenium modified nucleosides, nucleotides and nucleic acids
Author: Conlon, P., Jul 2021Supervisor: Vyle, J. (Supervisor) & Hale, K. (Supervisor)
Student thesis: Doctoral Thesis › Doctor of Philosophy