17512-84-4Relevant articles and documents
Structure correlation study of the beckmann rearrangement: X-ray structural analysis and 13C-13C 1-bond coupling constant study of a range of cyclohexanone oxime derivatives
Yeoh, Shin Dee,Harris, Benjamin L.,Simons, Tristan J.,White, Jonathan M.
experimental part, p. 905 - 917 (2012/09/22)
The X-ray structures of a range of oxime derivatives (1 and 4), of cyclohexanone and 4-tert-butylcyclohexanone, where the electron demand of the oxygenated substituent on the oxime nitrogen (OR) is systematically varied were determined. It was established
Organoaluminum-Promoted Beckmann Rearrangement of Oxime Sulfonates
Maruoka, Keiji,Miyazaki, Tohru,Ando, Mamoru,Matsumura, Yasushi,Sakane, Soichi,et al.
, p. 2831 - 2843 (2007/10/02)
The Beckmann rearrangement of oxime sulfonates with simultaneous nucleophilic trapping of the intermediary iminocarbocation by organoaluminum reagents is described.This process provides a new and highly efficient route to imino thioethers, imino selenoethers, imino nitriles, and α-alkylated amines starting from oxime sulfonates by the use of dialkylaluminum thiolates, selenolates, diethylaluminum chloride-trimethylsilyl cyanide, and trialkylaluminum-diisobutylaluminum hydride systems, respectively.The present organoaluminum-promoted Beckmann rearrangement of oxime sulfonates has been successfully applied to the synthesis of naturally occuring alkaloids, pumiliotoxin C and solenopsin A and B, in stereoselective fashion.Moreover, α,α-dialkylation of amines can be realized by the successive treatment of oxime sulfonates with trialkylaluminum followed by allylic or propargylic Grignard reagents in synthetically useful yields.
