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6,6-Dicyanopentafulvenes: electronic structure and regioselectivity in [2 + 2] cycloaddition-retroelectrocyclization

Aaron D Finke1, Oliver Dumele, Michal Zalibera

  • 1Laboratory of Organic Chemistry, ETH Zurich, Hönggerberg, HCI, CH-8093 Zurich, Switzerland.

Journal of the American Chemical Society
|October 10, 2012
PubMed

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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