
%0 Journal Article
%A Baker, Robert W. 
%A Liu, Song 
%A Sargent, Melvyn V. 
%A Skelton, Brian W. 
%A White, Allan H. 
%T Regioselectivity in the Lithiation of 1,3-Disubstituted Arenes
%J Australian Journal of Chemistry
%D 1997/10/14
%V 50
%N 8
%P 831-840
%K 
%R https://doi.org/10.1071/C97016
%U https://www.publish.csiro.au/paper/C97016 
%X 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&#8242;-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&#8242;,N&#8242;-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. 
