Metalation reactions. : IV. Metalation of o-alkyl- and o,o′-dialkyl-substituted alkylthiobenzenes

Metalation of o-alkyl- and o,o′-dialkylsubstituted alkylthiobenzenes with n-butyllithium, in the presence and absence of TMEDA, has been investigated. The results showed that metalation at the thioalkyl carbon probably occurs by direct attack of the organolithium reagent, although a transmetalation...

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Published inJournal of organometallic chemistry Vol. 178; no. 2; pp. 291 - 300
Main Authors Cabiddu, S., Melis, S., Piras, P.P., Sotgiu, F.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 02.10.1979
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Summary:Metalation of o-alkyl- and o,o′-dialkylsubstituted alkylthiobenzenes with n-butyllithium, in the presence and absence of TMEDA, has been investigated. The results showed that metalation at the thioalkyl carbon probably occurs by direct attack of the organolithium reagent, although a transmetalation reaction cannot be excluded in some cases. It has also been found that benzylic, thio-methylic, and ring metalation occurs in ether alone, whereas mainly thio-methylic or ring metalation occurs in the presence of TMEDA.
ISSN:0022-328X
1872-8561
DOI:10.1016/S0022-328X(00)94217-7