Synthesis of 1-aryl-1-phenylpropenes using an alkylation-rearrangement-methylation-isomerization one-pot reaction sequence.

Autor: Maraš, Nenad, Perdih, Franc, Kočevar, Marijan
Zdroj: Central European Journal of Chemistry; Oct2011, Vol. 9 Issue 5, p904-909, 6p
Abstrakt: ( Z/E)-1-(2-Methoxyaryl)-1-phenylpropenes have been prepared in good yields by heating a mixture of a phenolic substrate, cinnamyl chloride, tetramethylammonium chloride and KCO3 in polyethyleneglycol at 180°C. The one-pot synthesis proceeds through four discrete reaction steps: alkylation of the phenol with cinnamyl chloride, Claisen rearrangement, O-methylation and double-bond migration. The configuration of one crystalline product was determined using a single-crystal X-ray diffraction analysis. The thermodynamic and structural features of the products were evaluated using computational chemistry techniques. [InlineMediaObject not available: see fulltext.] [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index