tertButoxide
tert-butoxide is the tert-butoxide anion, (CH3)3CO−, the conjugate base of tert-butanol. It is most commonly encountered as its salts, especially potassium tert-butoxide (KOtBu) and sodium tert-butoxide (NaOtBu). These reagents are widely used as strong, bulky bases in organic synthesis.
Preparation and handling: tert-Butoxides are typically prepared by deprotonating tert-butanol with a strong base or via
Properties: The tert-butoxide anion is a strong, non-nucleophilic base due to steric hindrance from the tert-butyl
Applications: KOtBu and NaOtBu are used to generate enolates from carbonyl compounds, promote eliminations (E2) over
Safety: tert-Butoxides react with water and air, forming tert-butanol and corresponding hydroxide salts; they are caustic