1453841-14-9Relevant academic research and scientific papers
[2.2]Paracyclophane-Bis(triazole) Systems: Synthesis and Photochemical Behavior
Bahrin, Lucian G.,Sarbu, Laura G.,Jones, Peter G.,Birsa, Lucian M.,Hopf, Henning
, p. 12338 - 12345 (2017)
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.
Planar chiral triazole-based phosphanes derived from [2.2]paracyclophane and their activity in suzuki coupling reactions
Glover, Jean E.,Martin, David J.,Plieger, Paul G.,Rowlands, Gareth J.
, p. 1671 - 1675 (2013/04/10)
In this communication we report the short synthesis of a variety of planar chiral triazole-based phosphanes. These molecules have been readily prepared from 4-azido[2.2]paracyclophane in two steps. It was observed that the stability of the resulting phosphanes was dependent on the C-4 substituent. The efficacy of the new phosphanes in the palladium-mediated Suzuki-Miyaura coupling reaction was evaluated. The phosphanes proved to be more effective than previously prepared planar chiral [2.2]paracyclophane-based phosphanes. Planar chiral phosphanes have been prepared from the first example of a [2.2]paracyclophane- derived 1,2,3-triazole with a carbon substituent at the 4-position. The nature of the 4-substituent appears to control the stability of the resulting 1,4,5-trisubstituted triazoles. The activities of the phosphanes as ligands in Suzuki coupling reactions has also been assessed. Copyright
