60227-39-6Relevant articles and documents
Catalytic Functionalization of Styrenyl Epoxides via 2-Nickela(II)oxetanes
Desnoyer, Addison N.,Geng, Jialing,Drover, Marcus W.,Patrick, Brian O.,Love, Jennifer A.
supporting information, p. 11509 - 11512 (2017/08/30)
Low-valent nickel is shown to preferentially isomerize mono- or disubstituted epoxides into their corresponding aldehydes. Experiments with tetrasubstituted epoxides demonstrate that these reactions proceed via reactive 2-nickelaoxetane intermediates, and
An alternative reaction outcome in the gold-catalyzed rearrangement of 1-alkynyloxiranes
Gonzalez, Maria J.,Gonzalez, Jesus,Vicente, Ruben
supporting information, p. 6140 - 6143,4 (2020/09/16)
The gold(III)-catalyzed rearrangement of tetrasubstituted 1-alkynyloxiranes is described. This transformation led to a different reaction outcome with respect to related substrates previously studied. Thus, tertiary α-alkynylketones or alkynols can be selectively obtained. Moreover, gold(III) proved capable to catalyze the rearrangement of simple epoxides. These results indicate that gold(III) complexes act as oxophilic Lewis acids rather than π-acids in these transformations.
Reactivity and Selectivity in the Oxidation of Styrene Derivatives. IV. Studies on the Oxidation of Substituted β,β-Dimethylstyrenes
Suprun
, p. 247 - 255 (2007/10/03)
The liquid phase oxidation of substituted (p-MeO-, p-Cl-, m-CF3-) 2-aryl-3-methyl-but-2-enes, of 1,1-diphenyl-2-methyl-propene, of 1-ethoxy-2-methyl-1-phenyl-propene and of 9-isopropylidene-fluorene with pure oxygen was investigated in chlorobenzene solution and in presence of cumene and of cumene hydroperoxide in the temperature range 65-125°C. The product yields were determined gaschromatographically. The differences of the activation energies of epoxide formation and the parallel reactions were calculated. They amount to 19-48 kJ/mol. The epoxide selectivity increases with increasing temperature and increasing concentration of olefin. The relative chain propagation constants (kpC=C) were determined by competitive oxidation with cumene. The kpC=C values of substituted β,β-dimethylstyrenes can be correlated by a LFE-relationship with the ionisation energies of the olefins.
