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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

    Photochemistry of allenyl salicylaldehydes

    Birbaum, Frédéric ; Neels, Antonia ; Bochet, Christian G.

    In: Organic Letters, 2008, vol. 10, no. 15, p. 3175–3178

    The intramolecular photocycloaddition of aryl aldehydes containing allene side chains is a versatile reaction as it provides a rapid and efficient access to original complex structures such as 1,3,4-tetrahydro-1,4-epoxy-5-alkylidene-2-benzoxepines 2 and substituted 2-oxa-tricyclo[5.2.2.0]1,5undeca-4,8,10-triene-9-carbaldehydes 3. Novel polycyclic structures are...