Alkali Metal O,O-Diethyl Phosphorotelluroates, a Reagent Class for Deoxygenation of Epoxides, Especially Terminal Epoxides

Article abstract of DOI:10.1021/jo01300a016

Epoxides are deoxygenated to olefins by alkali metal O,O-diethyl phosphorotelluroates.These reagents can be used in stoichiometric quantities or they can be generated continuously in situ from tellurium under conditions that approach a catalytic nature with respect to the metal.Terminal epoxides are deoxygenated most readily, but the reaction does work for other types.In the case of epoxides formally derived from acyclic olefins, the Z compound reacts more easily than the E isomer and the deoxygenation is stereospecific. 1,2-Epoxycyclohexanes react faster than 1,2-epoxycyclopentanes.Selective deoxygenations, especially those in favor of terminal epoxides, are possible.