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https://hdl.handle.net/2440/17814
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Type: | Journal article |
Title: | A cyclodextrin molecular reactor for the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles |
Author: | Barr, L. Lincoln, S. Easton, C. |
Citation: | Supramolecular Chemistry, 2005; 17(7):547-555 |
Publisher: | Gordon Breach Sci Publ Ltd |
Issue Date: | 2005 |
ISSN: | 1061-0278 1029-0478 |
Statement of Responsibility: | Lorna Barr, Stephen F. Lincoln And Christopher J. Easton |
Abstract: | 6A-Deoxy-6A-propynamido-β-cyclodextrin reacts with 4-tert-butylphenyl azide in aqueous solution, to form the 5-(aminocarbonyl)-substituted triazole in preference to the 4-(aminocarbonyl)- substituted analogue, in a ratio of 25:1. The cyclodextrin moiety templates the reaction through the formation of a host-guest complex of the dipole with the dipolarophile, controlling the regio-selectivity of cycloaddition. In a control reaction under similar conditions, with propiolamide instead of the cyclodextrin derivative, 5- and 4-(aminocarbonyl)-1-(4-tert-butylphenyl)-1,2,3-triazole were formed in a ratio of 1:4. As well as reversing the regioselectivity, the cyclodextrin substituent increases the rate of cycloaddition, by at least two orders of magnitude for the reaction to give the 5-substituted cycloadduct. Even the rate of formation of the 4-substituted cycloadduct is increased by a factor of two. Less marked effects are observed with phenyl azide and 4-tert-butylbenzyl azide as dipoles. © 2005 Taylor & Francis. |
Keywords: | Molecular reactors Triazoles Cyclodextrins Regio selectivity Cycloadditions Templates |
DOI: | 10.1080/10610270500329131 |
Published version: | http://dx.doi.org/10.1080/10610270500329131 |
Appears in Collections: | Aurora harvest 2 Chemistry publications Environment Institute publications |
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