A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane

We report a green and convenient protocol to prepare 4,7,12,15-tetrachloro[2.2]paracyclophane, the precursor of parylene D, from 2,5-dichloro-p-xylene. In the first bromination step, with H(2)O(2)–HBr as a bromide source, this procedure becomes organic-waste-free and organic-solvent-free and can app...

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Detalles Bibliográficos
Autores principales: Pan, Donghui, Wang, Yanbin, Xiao, Guomin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238561/
https://www.ncbi.nlm.nih.gov/pubmed/28144311
http://dx.doi.org/10.3762/bjoc.12.237
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author Pan, Donghui
Wang, Yanbin
Xiao, Guomin
author_facet Pan, Donghui
Wang, Yanbin
Xiao, Guomin
author_sort Pan, Donghui
collection PubMed
description We report a green and convenient protocol to prepare 4,7,12,15-tetrachloro[2.2]paracyclophane, the precursor of parylene D, from 2,5-dichloro-p-xylene. In the first bromination step, with H(2)O(2)–HBr as a bromide source, this procedure becomes organic-waste-free and organic-solvent-free and can appropriately replace the existing bromination methods. The Winberg elimination–dimerization step, using aqueous sodium hydroxide solution instead of silver oxide for anion exchange, results in a significant improvement in product yield. Furthermore, four substituted [2.2]paracyclophanes were also prepared in this convenient way.
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spelling pubmed-52385612017-01-31 A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane Pan, Donghui Wang, Yanbin Xiao, Guomin Beilstein J Org Chem Full Research Paper We report a green and convenient protocol to prepare 4,7,12,15-tetrachloro[2.2]paracyclophane, the precursor of parylene D, from 2,5-dichloro-p-xylene. In the first bromination step, with H(2)O(2)–HBr as a bromide source, this procedure becomes organic-waste-free and organic-solvent-free and can appropriately replace the existing bromination methods. The Winberg elimination–dimerization step, using aqueous sodium hydroxide solution instead of silver oxide for anion exchange, results in a significant improvement in product yield. Furthermore, four substituted [2.2]paracyclophanes were also prepared in this convenient way. Beilstein-Institut 2016-11-17 /pmc/articles/PMC5238561/ /pubmed/28144311 http://dx.doi.org/10.3762/bjoc.12.237 Text en Copyright © 2016, Pan et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Pan, Donghui
Wang, Yanbin
Xiao, Guomin
A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane
title A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane
title_full A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane
title_fullStr A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane
title_full_unstemmed A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane
title_short A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane
title_sort new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238561/
https://www.ncbi.nlm.nih.gov/pubmed/28144311
http://dx.doi.org/10.3762/bjoc.12.237
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