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Updated: Jan 20, 2026
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols
Natalie J Capel1, Martin R Lindley1, Gareth J Pritchard1
1School of Science, Department of Chemistry, and School of Sports Exercise and Health Science, Loughborough University, Loughborough, Leicestershire LE11 3TU, U.K.
Abstract:
An indium-mediated isomerization of 1,4-dienols to 1,3-dienols is described. This procedure consists of the addition of pentadienylindium, in a protic solvent, to aldehydes giving the kinetic γ-allylation product in high yields. The subsequent conversion of this γ-allylation product to its thermodynamic 1,3-dienol α-isomer can be achieved by its exposure to indium triflate in the presence of a substoichiometric amount of aldehyde at room temperature. This transformation exhibited moderate to good substrate scope and has been shown to proceed by a 2-oxonia Cope rearrangement.
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