4372-77-4Relevant articles and documents
Organolithium addition to styrene and styrene derivatives: Scope and limitations
Wei, Xudong,Johnson, Paul,Taylor, Richard J.K.
, p. 1109 - 1116 (2000)
Styrene and a range of aryl-substituted styrene derivatives are shown to undergo efficient carbolithiation-trapping reactions in diethyl ether at -78 to -25 °C. The reactivities of different types of organolithium reagents were found to be: tertiary, secondary > primary; ? alkenyl, methyl, phenyl. Electron donating groups (e.g. methoxy and dialkylamino) at the ortho- or para- positions of the benzene ring deactivate the double bond towards organolithium addition, but their reactions with butyllithium can be facilitated by using TMEDA as co-solvent. 2-Benzyloxystyrene and 2-allyloxystyrene undergo efficient carbolithiation at -78 °C, but at room temperature alkyl transfer occurs, generating the corresponding alkylated phenol. 2-Vinylnaphthalene also undergoes carbolithiation-carboxylation in reasonable yield.
Organolithium additions to styrene are synthetically viable
Wei, Xudong,Taylor, Richard J. K.
, p. 187 - 188 (2007/10/03)
In diethyl ether at -78 to -25°C, styrene undergoes efficient addition reactions with a range of alkyllithium reagents, and the intermediate benzyllithiums can be trapped (e.g. with carbon dioxide and chlorotrimethylsilane); two aryl-substituted styrenes are shown to react in a similar manner.
