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Beilstein J. Org. Chem. 2015, 11, 1865–1875, doi:10.3762/bjoc.11.200
Graphical Abstract
Scheme 1: Proposed mechanism for the selenocyclization of model substrate 1.
Scheme 2: 5-Exo pathway of the proposed mechanism with all possible intermediates and products.
Figure 1: 1H NMR monitoring of the cyclization of 5-alkenylhydantoin 1 with PhSeCl in acetonitrile-d3 solutio...
Figure 2: Optimized geometries of possible Markovnikov-type intermediates formed by the anti-stereospecific a...
Figure 3: Energy profile for the proposed mechanism of selenocyclization of model substrate 1. Relative energ...
Figure 4: Optimized geometries for seleniranium cations and corresponding transition states for the formation...
Figure 5: Optimized geometries of intermediate bicyclic imidazolinium cations. The crucial bond lengths are g...
Figure 6: Optimized geometries of possible products of the selenocyclization of 1, with relative free energy ...
Scheme 3: Proposed mechanism for selenocyclization of model substrate 3.
Figure 7: Optimized geometries of possible intermediates of the selenocyclization of model substrate 3, with ...
Figure 8: Optimized geometries of possible products of the selenocyclization of model substrate 3, with relat...