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Synthesis 1998; 1998(1): 89-93
DOI: 10.1055/s-1998-1993
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Reactions of β-Ethylsulfanylpropionyl Tetrafluoroborate with Electron-Rich Aromatics: A Novel Synthesis of Aryl Vinyl Ketones

Mikhail V. Lebedev* , Valentine G. Nenajdenko, Elizabeth S. Balenkova
  • *Department of Chemistry, Moscow State University, 119899 Moscow, Russia; Fax + 7(0 95)9 32 88 46; E-mail: Nen@acylium.chem.msu.su
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Publikationsdatum:
31. Dezember 2000 (online)

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A new synthesis of aryl vinyl ketones is described. The acylation of active aromatics with the complex of β-ethylsulfanylpropionyl fluoride 1 and boron trifluoride leads to formation of 1-aryl-3-(ethylsulfanyl)propan-1-ones. Subsequent methylation with methyl triflate and elimination with an aqueous solution of KHCO3 results in formation of aryl vinyl ketones in 86-99% yield.

acylation - aryl vinyl ketone - β-ethylthiopropionyl fluoride

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