Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 17, Pages 8435-8439Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo501324w
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Funding
- Deutsche Forschungsgemeinschaft [Schm 647/18-1]
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A mechanistic study of the thermal Garratt-Braverman/[1,5]-H shift of ene-diallene 6 leading to alkenes (E)-8 and (Z)-8 is reported. The product ratio was found to be temperature-independent and does not agree with the computed energy barriers (i.e., TS2(E)double dagger and TS2(Z)double dagger). On the basis of experimental and DFT computational results, we propose a mechanism that is strongly controlled by nonstatistical dynamic effects.
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