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https://hdl.handle.net/2440/17918
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Type: | Journal article |
Title: | Effect of cyclodextrins on electrophilic aromatic bromination in aqueous solution |
Author: | Dumanski, P. Easton, C. Lincoln, S. Simpson, J. |
Citation: | Australian Journal of Chemistry: an international journal for chemical science, 2003; 56(11):1107-1111 |
Publisher: | CSIRO Publishing |
Issue Date: | 2003 |
ISSN: | 0004-9425 |
Statement of Responsibility: | Dumanski, Paul G ; Easton, Christopher J ; Lincoln, Stephen F ; Simpson, Jamie S |
Abstract: | Cyclodextrins act as molecular reactors to change the ratios of the products of reactions of anisole, acetanilide, 3-methylanisole, and 3-methylacetanilide with pyridinium dichlorobromate. With anisole and acetanilide, bromination at the para position is favoured over ortho substitution, and the effect is greatest with α-cyclodextrin. In the reactions of the methylanisole and methylacetanilide, the cyclodextrins afford higher yields of monobrominated products and less of the di- and tribromides, and β-cyclodextrin has the greatest effect. These outcomes can be attributed to inclusion of the substrates within the cyclodextrins restricting access of the reagent adjacent to the methoxy and acetamido groups. The yields of 4-bromoanisole, 4-bromoacetanilide, 4-bromo-3-methylanisole, and 4-bromo-3-methylacetanilide are thus increased from 73 to 94, 55 to 98, 37 to 86, and 39 to 72%, respectively. Perhaps more significantly, the quantities of the corresponding by-products are substantially reduced, from 27 to 6, 45 to 2, 63 to 14, and 61 to 28%. Since the reactions occur readily in water at ambient temperature, the cyclodextrins make them very efficient. |
Rights: | © CSIRO 2003 |
DOI: | 10.1071/CH03102 |
Published version: | http://dx.doi.org/10.1071/ch03102 |
Appears in Collections: | Aurora harvest 2 Chemistry publications Environment Institute publications |
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