Abstract
An improved, large scale synthesis of 5,8-bis(trimethylsilyl)cycloocta-1,3,6-triene is described. The compound may be deprotonated with n-butyllithium/THF or n-butyllithium/TMEDA to afford stable dilithium salts of the 1,4-bis(trimethylsilyl)cyclooctatetraenyl dianion, which may be oxidised with mercuric chloride to give free bis(trimethylsilyl)cyclooctatetraene as a mixture of the 1,4- and 1,6-isomers. Treatment of the bis(trimethylsilyl)cyclooctatetraenyl dianion with an excess of chlorotrimethylsilane gives 2,5,5,8-tetrakis(trimethylsilyl)cycloocta-1,3,6-triene.
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