Ortho-Directed Lithiation of omega-Phenoxy Alcohols.
omega-Phenoxy alcohols, PhO(CH(2))(n)()OH (n = 2-7), have been subjected to metalation with 2 equiv of n-butyllithium in tetrahydrofuran/methylcyclohexane solvent. Reaction of the resulting lithiated compounds with carbon dioxide (n = 2-7), benzaldehyde (n = 2-6), benzophenone (n = 2, 3), dimethylformamide (n = 2), ethyl formate (n = 2), and chlorodiphenylphosphine (n = 3) afforded the corresponding ortho-substituted hydroxyalkoxybenzenes in yields ranging from 45 to 83%. The synthesis is also reported of five new bis[o-(omega-hydroxyalkoxy)phenyl]mercury compounds (n = 2-6), four crystal structures of which have been determined.
Salteris
Constantinos S.
CS
Institute of Materials Science, NCSR "Democritos", 153 10 Aghia Paraskevi Attikis, Greece.
Kostas
Ioannis D.
ID
Micha-Screttas
Maria
M
Heropoulos
George A.
GA
Screttas
Constantinos G.
CG
Terzis
Aris
A