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Selective synthesis of 1,4-dialkylbenzenes from terephthalic acid

  • Terephthalic acid reacts with alkyl halides under Birch conditions to substituted 1,4-cyclohexadienes in high yields and good stereoselectivities. Electrophiles containing ester or nitrile groups undergo a surprising fragmentation under the reaction conditions. Subsequent treatment with chlorosulfonic acid proceeds by an interesting tandem decarbonylation/decarboxylation, affording 1,4-dialkylbenzenes in excellent regioselectivity. Thus our new method is superior to classical Friedel-Crafts alkylations.

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Metadaten
Author:Andrea Bramborg, Torsten LinkerORCiDGND
URL:http://www3.interscience.wiley.com/cgi-bin/jhome/77002176
DOI:https://doi.org/10.1002/adsc.201000322
ISSN:1615-4150
Document Type:Article
Language:English
Year of first Publication:2010
Year of Completion:2010
Release Date:2017/03/25
Source:Advanced synthesis & catalysis. - ISSN 1615-4150. - 352 (2010), 13, S. 2195 - 2199
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert