66691-27-8Relevant articles and documents
Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation
Chang, Xihao,Zhang, Qinglin,Guo, Chang
, p. 10 - 13 (2019/01/04)
A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochemical transformation, furnishing the corresponding amides in up to 86% yield.
Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement
Hossian, Asik,Jana, Ranjan
, p. 9768 - 9779 (2016/10/31)
We report herein, a silver(i)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen. Mechanistically, the aryl ether moiety undergoes an intramolecular ipso attack by the carboxyl radical followed by a C-O or C-S bond cleavage. Aryl-2-mercaptobenzoates undergo oxidative dimerization through a thiol moiety in situ.
Self-assembling chiral metallo-clefts; synthesis and molecular structure of N,N'-bis(12H-benzoxanthen-12-ylidene)-1,2-ethanediamine zinc(II)-dichloride complex
Barf, Tjeerd,Jansen, Johan F. G. A.,Bolhuis, Fre van,Spek, Anthony L.,Feringa, Ben L.
, p. 376 - 383 (2007/10/02)
Bulky ligands for cleft-type metal complexes were synthesized from thioketones and diamines in yields varying from 20 - 80 percent.A molecular structure determination of one ligand, N,N'-bis(12H-benzoxanthen-12-ylidene)-1,2-propanediamine (19), was performed.A metallo-cleft was constructed by a self-assembling process with zinc(II) chloride.A crystallographic study of this zinc complex (24) revealed surprisingly that an anti-syn inversion of the imine moieties of the ligand had taken place during complexation.