Journal of Organometallic Chemistry p. 193 - 210 (1987)
Update date:2022-08-18
Topics:
Akita, M.
Matsuoka, K.
Asami, K.
Yasuda, H.
Nakamura, A.
The reactions of zirconium-diene complexes, ZrCp2(s-cis-diene), with bifunctional electrophiles, i.e. α,β-unsaturated ketones, unsaturated esters and substituted oxacyclopropanes were investigated.Reaction of ZrCp2(s-cis-isoprene) with an equivalent of 3-buten-2-one or alkyl acrylates, selectively gives 1,2-addition products.C-C bond formation occurred at the C(1) atom of the isoprene moiety whereas 1,3-pentadiene, 2-methyl-1,3-pentadiene- and 2,4-dimethyl-1,3-pentadiene complexes induced the regioselective 1,2-addition at the C(4) position of the diene moiety.Phenyloxacyclopropane and 2-methyl-3-phenyl-oxacyclopropane also react with ZrCp2(isoprene) leading to C-C bond formation from the C(1) atom of isoprene to the oxirane carbon bearing the phenyl group.The corresponding reactions of 2-methyl-2-butene-1,4-diylmagnesium with α,β-unsaturated carbonyl compounds were also studied and found to give quite different products.
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