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Synthesis 2001; 2001(3): 0431-0436
DOI: 10.1055/s-2001-11435
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Halogenation of β-Alkoxyvinyl Polyhaloalkyl Ketones: A Convenient Route for the Synthesis of α-Chloro- or α-Bromo-β-alkoxyvinyl Polyhaloalkyl Ketones

Igor I. Gerus* , Liliya M. Kacharova, Sergei I. Vdovenko
  • *Institute of Bioorganic Chemistry, Ukrainian National Academy of Sciences, Str. Murmanskaya 1, Kiev, 02094, Ukraine; Fax + 38(0 44)5 73 25 52; E-mail: igerus@alfacom.com
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Publication Date:
31 December 2001 (online)

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A number of α-chloro- and α-bromo-β-alkoxyvinyl polyhaloalkyl ketones 4 and 5 were synthesized in high yields by halogenation of β-alkoxyvinyl polyhaloalkyl ketones 1 with chlorine or bromine and further dehydrohalogenation of dihalo-intermediates 2 and 3 with pyridine. The Z configuration of ketones 4 and 5 was deduced from X-ray analysis and NMR spectra. Some typical nucleophilic reactions of the title compounds 4 and 5 with amines were carried out to check their reactivity.

enones - halogenation - electrophilic additions - eliminations - aminations