Conversion of 1,4-diketones into para-disubstituted benzenes.
J Org Chem
; 75(23): 8024-38, 2010 Dec 03.
Article
em En
| MEDLINE
| ID: mdl-21067209
ABSTRACT
Reaction of acetylides with aldehydes to form but-2-yne-1,4-diols, followed by triple bond reduction and oxidation of the hydroxyl groups, gives 1,4-diketones; these react with vinyllithium, and the resulting diols undergo ring-closing metathesis to form 2-cyclohexene-1,4-diols. Dehydration, usually by acid treatment, then gives benzenes carrying substituents in a 1,4 relationship. Use of substituted vinyllithiums provides further substitution on the final benzene rings. The method can be applied to the synthesis of C5-aryl carbohydrates.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2010
Tipo de documento:
Article
País de afiliação:
Canadá