TY - JOUR
T1 - Directed lithiation of some chroman-4-ols
AU - Bethune, Richard J.
AU - Gabbutt, Christopher D.
AU - Guinot, Stéphane G R
AU - Hepworth, John D.
AU - Heron, B. Mark
PY - 1994/12/1
Y1 - 1994/12/1
N2 - Directed lithiation of chroman-4-ols occurs predominantly at C-5 under kinetic control, but at C-8 at higher temperatures. Dehydration and oxidation of the products provides viable routes to 5-substituted 2H-chromenes and chroman-4-ones, respectively. The chroman-4-ones have been converted into novel pyrano[4,3,2-de]phthalazines. 2,2,5,7-Tetramethylchroman-4-ol is preferentially lithiated at the 5-methyl group and leads to the pyrano[2,3,4-de] [1]benzopyran system.
AB - Directed lithiation of chroman-4-ols occurs predominantly at C-5 under kinetic control, but at C-8 at higher temperatures. Dehydration and oxidation of the products provides viable routes to 5-substituted 2H-chromenes and chroman-4-ones, respectively. The chroman-4-ones have been converted into novel pyrano[4,3,2-de]phthalazines. 2,2,5,7-Tetramethylchroman-4-ol is preferentially lithiated at the 5-methyl group and leads to the pyrano[2,3,4-de] [1]benzopyran system.
UR - http://www.scopus.com/inward/record.url?scp=37049081020&partnerID=8YFLogxK
U2 - 10.1039/P19940001925
DO - 10.1039/P19940001925
M3 - Article
AN - SCOPUS:37049081020
SP - 1925
EP - 1933
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
SN - 0300-922X
IS - 14
ER -