Conformer-specific polar cycloaddition of dibromobutadiene with trapped propene ions

Ardita Kilaj, Jia Wang, Patrik Straňák, Max Schwilk, Uxía Rivero, Lei Xu, O. Anatole Lilienfeld, Jochen Küpper () and Stefan Willitsch ()
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Ardita Kilaj: University of Basel
Jia Wang: Deutsches Elektronen-Synchrotron DESY
Patrik Straňák: University of Basel
Max Schwilk: University of Basel
Uxía Rivero: University of Basel
Lei Xu: University of Basel
O. Anatole Lilienfeld: University of Basel
Jochen Küpper: Deutsches Elektronen-Synchrotron DESY
Stefan Willitsch: University of Basel

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract Diels–Alder cycloadditions are efficient routes for the synthesis of cyclic organic compounds. There has been a long-standing discussion whether these reactions proceed via stepwise or concerted mechanisms. Here, we adopt an experimental approach to explore the mechanism of the model polar cycloaddition of 2,3-dibromo-1,3-butadiene with propene ions by probing its conformational specificities in the entrance channel under single-collision conditions in the gas phase. Combining a conformationally controlled molecular beam with trapped ions, we find that both conformers of the diene, gauche and s-trans, are reactive with capture-limited reaction rates. Aided by quantum-chemical and quantum-capture calculations, this finding is rationalised by a simultaneous competition of concerted and stepwise reaction pathways, revealing an interesting mechanistic borderline case.

Date: 2021
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DOI: 10.1038/s41467-021-26309-5

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