tertbutoxides

Tert-butoxides are a class of chemical compounds characterized by the tert-butyl group (C(CH3)3) attached to an oxygen atom, which is in turn bonded to a metal cation. The most common examples include potassium tert-butoxide (KOtBu) and sodium tert-butoxide (NAtBu). These compounds are typically white crystalline solids, though their solubility and appearance can vary depending on the specific metal.

The tert-butoxide anion, (CH3)3CO-, is a strong, sterically hindered base. The bulky tert-butyl group prevents it from acting as a nucleophile in many reactions, making it a highly selective base. This property is particularly valuable in organic synthesis, where it is used to deprotonate weakly acidic protons, often at alpha-carbons of carbonyl compounds, or in elimination reactions to form alkenes. Potassium tert-butoxide is a widely used reagent in reactions such as the Williamson ether synthesis and various condensation reactions. Sodium tert-butoxide exhibits similar reactivity. Due to their strong basicity and tendency to absorb moisture, tert-butoxides are often handled under inert atmosphere conditions. They are typically prepared by reacting tert-butyl alcohol with an alkali metal, such as potassium or sodium, or their hydrides.