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Sequential enyne cross-metathesis reactions of arylalkynes with ethylene followed by atom transfer radical addition (ATRA) with ethyl dichloroacetate or dichloroacetonitrile provide 1,5-dichloropent-2-ene derivatives. The second-generation Grubbs alkylidene complex [RuCl2(=CHPh)(PCy3)(NHC)] [NHC = 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene] is used as the catalyst precursor for both reactions. Preliminary results show that the reaction products can be converted into vinylcyclopropanes by dechlorination with magnesium or manganese.
Harald Brune, Roland Hany, Roland Widmer, Michael Bauer, Samuel Thomas Stolz