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1 article(s) from Marković, Zoran S.

Mechanism, kinetics and selectivity of selenocyclization of 5-alkenylhydantoins: an experimental and computational study

Biljana M. Šmit,
Radoslav Z. Pavlović,
Dejan A. Milenković and
Zoran S. Marković

Beilstein J. Org. Chem. 2015, 11, 1865–1875, doi:10.3762/bjoc.11.200

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Graphical Abstract

Scheme 1: Proposed mechanism for the selenocyclization of model substrate 1.

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Scheme 2: 5-Exo pathway of the proposed mechanism with all possible intermediates and products.

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Figure 1: ¹H NMR monitoring of the cyclization of 5-alkenylhydantoin 1 with PhSeCl in acetonitrile-d₃ solutio...

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Figure 2: Optimized geometries of possible Markovnikov-type intermediates formed by the anti-stereospecific a...

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Figure 3: Energy profile for the proposed mechanism of selenocyclization of model substrate 1. Relative energ...

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Figure 4: Optimized geometries for seleniranium cations and corresponding transition states for the formation...

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Figure 5: Optimized geometries of intermediate bicyclic imidazolinium cations. The crucial bond lengths are g...

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Figure 6: Optimized geometries of possible products of the selenocyclization of 1, with relative free energy ...

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Scheme 3: Proposed mechanism for selenocyclization of model substrate 3.

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Figure 7: Optimized geometries of possible intermediates of the selenocyclization of model substrate 3, with ...

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Figure 8: Optimized geometries of possible products of the selenocyclization of model substrate 3, with relat...

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Published 07 Oct 2015

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