Me3OM

Me3OM, also known as tert-butoxide or t-butoxide, is a chemical compound. It is the conjugate base of tert-butanol. In its pure form, it is a white solid. Me3OM is a strong base and a nucleophile, making it useful in organic synthesis. It is commonly used as a reagent in reactions such as deprotonation and elimination. The tert-butoxide anion, [ (CH3)3CO ]-, is a bulky species due to the presence of the three methyl groups attached to the central carbon atom. This steric hindrance influences its reactivity, often favoring elimination reactions over substitution reactions in certain contexts. Me3OM is typically prepared by reacting tert-butanol with a strong base such as sodium hydride or potassium metal. It is often encountered as its alkali metal salts, such as potassium tert-butoxide (KOtBu) or sodium tert-butoxide (NaOtBu). These salts are readily available commercially and are widely employed in laboratory settings. When dissolved in appropriate solvents like tetrahydrofuran or dimethyl sulfoxide, Me3OM can effectively abstract protons from a variety of organic molecules. Its applications span across various synthetic transformations, including the formation of enolates, the preparation of ethers, and as a catalyst in polymerization reactions. Care should be taken when handling Me3OM due to its strong basicity and hygroscopic nature.