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Article Dans Une Revue Chemical Physics Letters Année : 2004

Theoretical study of the electrocyclization product of butadiyne: structure, stability and possible formations

Patrick Chaquin
Anthony Scemama

Résumé

The four-membered cyclic C4H2 resulting from electrocyclization of butadiyne has been found 75.2 kcal/mol above the latter species. In its ground state, it is a singlet non-planar biscarbene of C2 symmetry. The electronic structures of the singlet and triplet have been studied using ELF analysis. The opening into butadiyne needs ca. 20 kcal/mol activation and follows a pathway which does not preserve the C2 symmetry. Breaking the carbene-carbene bond results in a bicyclo-biscarbene, a degenerate isomerization which offers a reaction path for the scrambling of C2C3 atoms in butadiyne. Breaking the HC–C bond results in a sigmatropic shift yielding cyclopropylidene.

Dates et versions

hal-01539077 , version 1 (14-06-2017)

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Citer

Patrick Chaquin, Anthony Scemama. Theoretical study of the electrocyclization product of butadiyne: structure, stability and possible formations. Chemical Physics Letters, 2004, 394 (4-6), pp.244--249. ⟨10.1016/j.cplett.2004.06.106⟩. ⟨hal-01539077⟩
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