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Re2o7-Catalyzed Reaction Of Hemiacetals And Aldehydes With O-, S-, And C-Nucleophiles, Wantanee Sittiwong, Michael W. Richardson, Charles E. Schiaffo, Thomas J. Fisher, Patrick H. Dussault
Re2o7-Catalyzed Reaction Of Hemiacetals And Aldehydes With O-, S-, And C-Nucleophiles, Wantanee Sittiwong, Michael W. Richardson, Charles E. Schiaffo, Thomas J. Fisher, Patrick H. Dussault
Chemistry Department: Faculty Publications
Re(VII) oxides catalyze the acetalization, monoperoxyacetalization, monothioacetalization and allylation of hemiacetals. The reactions, which take place under mild conditions and at low catalyst loadings, can be conducted using hemiacetals, the corresponding O-silyl ethers, and, in some cases, the acetal dimers. Aldehydes react under similar conditions to furnish good yields of dithioacetals. Reactions of hemiacetals with nitrogen nucleophiles are unsuccessful. 1,2-Dioxolan-3-ols (peroxyhemiacetals) undergo Re(VII)-promoted etherification but not allylation. Hydroperoxyacetals (1-alkoxyhydroperoxides) undergo selective exchange of the alkoxide group in the presence of either Re2O7 or a Brønsted acid.
A New Peroxide Fragmentation: Efficient Chemical Generation Of 1O2 In Organic Media, Patrick Dussault, Prasanta Ghorai
A New Peroxide Fragmentation: Efficient Chemical Generation Of 1O2 In Organic Media, Patrick Dussault, Prasanta Ghorai
Chemistry Department: Faculty Publications
Monoactivated derivatives of 1,1-dihydroperoxides undergo an unprecedented base-promoted fragmentation to efficiently generate singlet oxygen (1O2) in anhydrous organic solvents.