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A pseudopericyclic [3,5]-sigmatropic rearrangement of a coumarin trichloroacetimidate derivative

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Abstract

Thermolysis of a coumarin trichloroacetimidate yields a single rearrangement product. The proposed mechanism is a pseudopericyclic allowed (Woodward–Hoffman forbidden) [3,5]-sigmatropic rearrangement to form the corresponding amide followed by a sigmatropic [1,5]-hydrogen migration. Transition state calculations at the B3LYP/6-31G(d,p) level support this mechanism and suggest the selectivity is influenced by the stability of the intermediates.

Graphical abstract: A pseudopericyclic [3,5]-sigmatropic rearrangement of a coumarin trichloroacetimidate derivative

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Publication details

The article was received on 19 Sep 2017, accepted on 26 Oct 2017 and first published on 27 Oct 2017


Article type: Communication
DOI: 10.1039/C7OB02335A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    A pseudopericyclic [3,5]-sigmatropic rearrangement of a coumarin trichloroacetimidate derivative

    T. Rajale, S. Sharma, D. K. Unruh, D. A. Stroud and D. M. Birney, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02335A

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