Organolithium addition to styrene and styrene derivatives: scope and limitations

Autor:	Xudong Wei, Richard J. K. Taylor, Johnson Paul David
Rok vydání:	2000
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Double bond Chemistry Reagent Butyllithium Organic chemistry Phenol Diethyl ether Alkylation Benzene Medicinal chemistry Styrene
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :1109-1116
ISSN:	1364-5463 1470-4358
DOI:	10.1039/a910195k
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::875e69702d4fdbe5d3dfb0eca4fd7326 https://doi.org/10.1039/a910195k Zobrazit plný text záznamu