69962-41-0Relevant articles and documents
A Phosphine-Mediated Dearomative Skeletal Rearrangement of Dianiline Squaraine Dyes
Bacher, Emily P.,Koh, Kevin J.,Lepore, Antonio J.,Oliver, Allen G.,Wiest, Olaf,Ashfeld, Brandon L.
supporting information, p. 2853 - 2857 (2021/05/05)
A phosphorus(III)-mediated dearomatization of ortho-substituted dianiline squaraine dyes results in an unusual skeletal rearrangement to provide exotic, highly conjugated benzofuranone and oxindole scaffolds bearing a C3 side chain comprised of a linear conflagration of an enol, a phosphorus ylide, and 2,4-disubstituted aniline. Employing experimental and computational analysis, a mechanistic evaluation revealed a striking dependence on the acidity of the aniline ortho substituent. Notably, the rearrangement adducts underwent rapid and complete reversion to the parent squaraine in the presence of a Br?nsted acid.
Assisted tandem catalytic RCM-aromatization in the synthesis of pyrroles and furans
Schmidt, Bernd,Krehl, Stefan,Jablowski, Eric
supporting information; experimental part, p. 5119 - 5130 (2012/08/07)
An assisted tandem catalytic transformation of diallyl amines and diallyl ethers into N-aryl pyrroles and furans, respectively, is described. The sequence relies on ring closing metathesis followed by dehydrogenation of the initially formed dihydropyrroles and dihydrofurans. Both steps are Ru-catalyzed, but the sequence requires only one precatalyst, because conversion of the metathesis catalyst into the dehydrogenation catalyst is achieved in situ, triggered by the oxidant tert-butyl hydroperoxide.