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Université de Fribourg

The photocycloaddition of arenes and allenes

Streit, Ursula ; Birbaum, Frédéric ; Quattropani, Anna ; Bochet, Christian G.

In: The Journal of Organic Chemistry, 2013, p. -

In the present work, we report on a new intramolecular para-cycloaddition of arenes with allenes, yielding attractive rigid scaffolds bearing several reactive functionalities to build in further diversity. Bicyclo[2.2.2]octadiene-type products and benzoxepine acetals are formed in this reaction, in ratios and yields depending on the substitution pattern on the aromatic ring, the nature of the...

Université de Fribourg

The arene–alkene photocycloaddition

Streit, Ursula ; Bochet, Christian G.

In: Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 525–542

n the presence of an alkene, three different modes of photocycloaddition with benzene derivatives can occur; the [2 + 2] or ortho, the [3 + 2] or meta, and the [4 + 2] or para photocycloaddition. This short review aims to demonstrate the synthetic power of these photocycloadditions.