Advanced Synthesis & Catalysis

Selective Synthesis of 1, 4??Dialkylbenzenes from Terephthalic Acid

A Bramborg, T Linker

Index: Bramborg, Andrea; Linker, Torsten Advanced Synthesis and Catalysis, 2010 , vol. 352, # 13 p. 2195 - 2199

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Citation Number: 5

Abstract

Abstract 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 ...