Oxidation with Selenium Dioxide
Selenium dioxide can perform several common types of oxidations, such as alcohols to ketones and aldehydes, as well as dehydrogenation of ketones to enones. Because of its toxicity, and the sometimes malodorous selenium-containing byproducts formed, SeO2 is used only where it competes well with other methods, or provides unique reactivity. One of these is the allylic oxidation of alkenes to allylic alcohols with regiocontrol (without migration of the double bond), and a second is the α-oxidation of ketones to α-diketones (only effective if there are no β-hydrogens).
Gyridinal: Meinwald, J. Tetrahedron Lett. 1973, 281. DOI
Bakkenolide-A: Reddy, D. S.. Org. Lett. 2004, 6, 3345. DOI
Hamigeran B: Trost, B. M.; Pissot-Soldermann, C.; Chen, I.; Schroeder, G. M. J. Am. Chem. Soc. 2004, 126, 4480. DOI
Semperviridine: Gribble, G. W.; Barden, T. C.; Johnson, D. A. Tetrahedron Lett. 1988, 44, 1988
