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Diels-Alder cycloadditions are efficient routes for the synthesis of cyclicorganic compounds. There has been a long-standing discussion whether thesereactions proceed via stepwise or concerted mechanisms. Here, we adopt a newexperimental approach to explore the mechanistic details of the model polarcycloaddition of 2,3-dibromo-1,3-butadiene with propene ions by probing itsconformational specificities in the entrance channel under single-collisionconditions in the gas phase. Combining a conformationally controlled molecularbeam with trapped ions, we find that both conformers of the diene, gauche ands-trans, are reactive with capture-limited reaction rates. Aided byquantum-chemical and quantum-capture calculations, this finding is rationalisedby a simultaneous competition of concerted and stepwise reaction pathways,revealing an interesting mechanistic borderline case.

Conformer-specific polar cycloaddition of dibromobutadiene with trapped propene ions