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[2.2]Paracyclophane-Bis(triazole) Systems: Synthesis and Photochemical Behavior. 2017

Lucian G Bahrin, and Laura G Sarbu, and Peter G Jones, and Lucian M Birsa, and Henning Hopf
Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.

Mono-, pseudo-gem, and pseudo-para ethynylcyclophanes and bis(azides) have been employed as addition partners in CuAAC reactions to design and build complex extended molecular scaffolds. The reactivity of the resulting triazoles was investigated under photochemical conditions. A variety of newly substituted [2.2]paracyclophanes were identified; deazotization of pseudo-gem and pseudo-para adducts provided indolophane derivatives. An intramolecular stabilization effect was observed in the case of pseudo-gem derivatives. A photochemical rearrangement from a pseudo-para adduct to a pseudo-ortho product was identified.

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