Author:
Baker Robert W.,Liu Song,Sargent Melvyn V.,Skelton Brian W.,White Allan H.
Abstract
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.
Cited by
10 articles.
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