Regioselectivity in the Lithiation of 1,3-Disubstituted Arenes

R.W. Baker, S. Liu, M.V. Sargent, Brian Skelton, Allan White

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8 Citations (Scopus)


The regioselectivity of the lithiation of 1,4,5,8-tetramethoxynaphthalene-2-carbaldehyde (7) with butyllithium or phenyllithium in the presence of N,N,N'-trimethylethylenediamine and the subsequent bromination of the lithiated species so generated with 1,2-dibromotetrafluoroethane were investigated. Similar investigations with butyllithium as base in the presence of N,N,N',N'-tetramethylethylenediamine or potassium t-butoxide were carried out on 1,4,5,8-tetramethoxynaphthalene-2-methanol (14). These studies were extended to 1,5,8-trimethoxynaphthalene-3-methanol (25), 3-methoxybenzenemethanol (29) and 3,5-dimethoxybenzenemethanol (32). The X-ray crystal structure of 6-bromo-1,4,5,8-tetramethoxynaphthalene-2-methanol (17) is described.
Original languageEnglish
Pages (from-to)831-840
JournalAustralian Journal of Chemistry: an international journal for chemical science
Publication statusPublished - 1997


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