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Control of the intramolecular [2+2] photocycloaddition in a bis-stilbene macrocycle

Yuewen Xu1, Mark D Smith, Jeanette A Krause

  • 1Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, USA.

The Journal of Organic Chemistry
|May 26, 2009
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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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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