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

• Authors: Nenad Maraš , Franc Perdih , Marijan Kočevar
• Languages of publication: EN

Abstracts

EN

(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 K2CO3 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. [...]

Keywords

EN

Tetramethylammonium; Phenols; Claisen rearrangement; Methylation; Atropisomerism

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2011
• Volume: 9
• Issue: 5
• Pages: 904-909

Dates

published

1 - 10 - 2011

online

24 - 7 - 2011

Contributors

author

Nenad Maraš

• Faculty of Chemistry and Chemical Technology, University of Ljubljana, SI-1000, Ljubljana, Slovenia

author

Franc Perdih

author

Marijan Kočevar

• Faculty of Chemistry and Chemical Technology, University of Ljubljana, SI-1000, Ljubljana, Slovenia

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Identifiers

DOI

10.2478/s11532-011-0074-y