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  1. 1 Open Chemistry

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  1. 1 2011

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  1. 1 Kočevar M.

  2. 1 Maraš N.

  3. 1 Perdih F.

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

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Maraš N., Perdih F., Kočevar M.
Open Chemistry
|
2011
|
vol. 9
|
issue 5
904-909
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. [...]
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