tbutoxide

tert-Butoxide refers to the conjugate base of tert-butanol, a tertiary alcohol. Its chemical formula is typically written as (CH3)3CO-. It is a strong, bulky base commonly used in organic chemistry reactions. The tert-butoxide anion is a nucleophile but is often employed primarily for its basicity due to the significant steric hindrance around the oxygen atom. This bulkiness makes it less likely to engage in nucleophilic substitution reactions compared to smaller alkoxide bases.

Commonly encountered tert-butoxide salts include potassium tert-butoxide (KOtBu) and sodium tert-butoxide (NaoTBu). Potassium tert-butoxide is particularly widely used. These salts are typically soluble in organic solvents such as tetrahydrofuran (THF) and dimethyl sulfoxide (DMSO).

In organic synthesis, tert-butoxide is frequently used for deprotonation reactions, such as the formation of enolates from ketones and esters. Its strong basicity allows for efficient deprotonation, while its steric bulk minimizes unwanted side reactions like nucleophilic attack on carbonyl carbons. It is also employed in elimination reactions, promoting the formation of alkenes by abstracting a proton. The choice between different tert-butoxide salts can depend on factors such as solubility and the specific requirements of the reaction.