
TY  - JOUR
A1  - Baker, Robert W. 
A1  - Liu, Song 
A1  - Sargent, Melvyn V. 
A1  - Skelton, Brian W. 
A1  - White, Allan H. 
T1  - Regioselectivity in the Lithiation of 1,3-Disubstituted Arenes
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1997
VL  - 50
IS  - 8
SP  - 831
EP  - 840
KW  - 
UR  - https://doi.org/10.1071/C97016 
N2  - 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. 
ER  -

