57429-67-1Relevant academic research and scientific papers
Radical-induced Ring Opening of Epoxides. A Convenient Alternative to the Wharton Rearrangement
Barton, Derek H. R.,Motherwell, Robyn S. Hay,Motherwell, William B.
, p. 2363 - 2367 (2007/10/02)
Tri-n-butyltin hydride reduction of an αβ-epoxy-O-thiocarbonylimidazolide derivative of an alcohol leads via oxiran ring-opening to the formation of an allylic alkoxyl radical.By a suitable choice of experimental conditions, this radical can either be quenched by hydrogen-atom transfer from the stannane or allowed to undergo further rearrangement.
Stereochemical Studies on the Nucleophilic Substitution in the Reaction of Allylic Phosphates with Organoaluminum Reagents
Itoh, Akira,Ozawa, Shuji,Oshima, Koichiro,Sasaki, Shizuka,Yamamoto,Hajime,et al.
, p. 2357 - 2362 (2007/10/02)
The reaction of cis- or trans-5-isopropenyl-2-methyl-2-cyclohexenyl diethyl phosphate (1) with Me2AlX (X= OPh, SPh, NHPh) in hexane results in substitution of the -O-PO(OEt)2 group with X under predominant inversion.In contrast, treatment of cis- or trans-1 with trialkylaluminum produces predominantly the allyl-nonallyl coupling products of the same (thermodynamically more stable) configuration.Similar alkylation of endo- and exo-2-acetoxynorcarane gave endo-2-methylnorcarane, exclusively.
