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A pseudopericyclic [3,5]-sigmatropic rearrangement of a coumarin trichloroacetimidate derivative.
Organic & Biomolecular Chemistry 2018 Februrary 8
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.
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