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• W2005463039 startingPage "2906" @default.
• W2005463039 abstract "Abstract A variety of 1,1,4,4‐tetraal kynylbutatrienes and 1,4‐dialkynylbutatrienes was synthezized by dimerization of the corresponding gem‐dibromoolefins. Both 1 H and 13 C NMR spectroscopy indicated that the di‐ and tetraalkynylated butatrienes are formed as a mixture of cis and trans isomers. Variable temperature NMR studies evidenced a facile cis–trans isomerization, thus preventing the separation of these isomers by gravity or high‐performance liquid chromatography (HPLC). For 1,1,4,4‐tetraalkynylbutatrienes, the activation barrier Δ G ≠ was measured by magnetization transfer to be around 20 kcal mol −1 , in the range of the barrier for internal rotation about a peptide bond. Unlike the tetraalkynylated [3]cumulenes, 1,4‐dialkynylbutatrienes are more difficult to isomerize and could, in one case, be obtained isomerically pure. Based on experimental data, the rotational barrier Δ G ≠ for 1,4‐dialkynylbutatrienes is estimated to be around 25 kcal mol −1 . The hypothesis of a stabilizing effect of the four alkynyl substituents on the proposed but‐2‐yne‐1,4‐diyl singlet diradical transition state of this cis–trans isomerization is further supported by a computational study." @default.
• W2005463039 created "2016-06-24" @default.
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• W2005463039 date "2004-06-15" @default.
• W2005463039 modified "2023-10-17" @default.
• W2005463039 title "Peralkynylated Buta-1,2,3-Trienes: Exceptionally Low Rotational Barriers of Cumulenic CC Bonds in the Range of Those of Peptide CN Bonds" @default.
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• W2005463039 doi "https://doi.org/10.1002/chem.200400218" @default.
• W2005463039 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/15214071" @default.
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