Download PDF
Synthesis 1998; 1998(1): 89-93
DOI: 10.1055/s-1998-1993
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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