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Regioselective bromination of 1,4-dimethoxy-2,3-dimethylbenzene and conversion into sulfur-functionalised benzoquinones

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Aitken_2016_TL_Regioselective_AAM.pdf (286.8Kb)
Date
11/03/2016
Author
Aitken, Robert Alan
Jethwa, Siddharth Janak
Richardson, Neville Vincent
Slawin, Alexandra Martha Zoya
Keywords
Bromination
Benzotrifluoride
Solvent effects
X-ray structures
QD Chemistry
DAS
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Abstract
The NBS bromination of 1,4-dimethoxy-2,3-dimethylbenzene has been examined under a variety of conditions in both 1,1,1-trichloroethane and benzotrifluoride. Four different bromination products have been isolated including the previously unknown 1-bromo-4-bromomethyl-2,5-dimethoxy-3-methylbenzene whose single crystal X-ray structure is presented. The synthetically useful 2,3-bis(bromomethyl)-1,4-dimethoxybenzene is readily prepared using either solvent and it has been converted into new sulfur-containing quinone derivatives
Citation
Aitken , R A , Jethwa , S J , Richardson , N V & Slawin , A M Z 2016 , ' Regioselective bromination of 1,4-dimethoxy-2,3-dimethylbenzene and conversion into sulfur-functionalised benzoquinones ' , Tetrahedron Letters , vol. 57 , no. 14 , pp. 1563-1566 . https://doi.org/10.1016/j.tetlet.2016.02.091
Publication
Tetrahedron Letters
Status
Peer reviewed
DOI
https://doi.org/10.1016/j.tetlet.2016.02.091
ISSN
0040-4039
Type
Journal article
Rights
Copyright © 2016 Elsevier Ltd. All rights reserved. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1016/j.tetlet.2016.02.091
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  • University of St Andrews Research
URL
http://www.sciencedirect.com/science/article/pii/S0040403916302003#appd002
URI
http://hdl.handle.net/10023/10376

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