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

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Central European Journal of Chemistry

Abstract

(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.

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Authors and Affiliations

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

    Nenad Maraš, Franc Perdih & Marijan Kočevar

  2. CO EN-FIST, SI-1000, Ljubljana, Slovenia

    Franc Perdih

Authors
  1. Nenad Maraš
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  2. Franc Perdih
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  3. Marijan Kočevar
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Correspondence to Marijan Kočevar.

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Maraš, N., Perdih, F. & Kočevar, M. Synthesis of 1-aryl-1-phenylpropenes using an alkylation-rearrangement-methylation-isomerization one-pot reaction sequence. cent.eur.j.chem. 9, 904–909 (2011). https://doi.org/10.2478/s11532-011-0074-y

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  • DOI: https://doi.org/10.2478/s11532-011-0074-y

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