Halogenation of β-alkoxyvinyl polyhaloalkyl ketones: A convenient route for the synthesis of α-chloro- or α-bromo-β-alkoxyvinyl polyhaloalkyl ketones

Article abstract of DOI:10.1055/s-2001-11435

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.