tertbutüülliitium

tert-Butyllithium, often abbreviated as t-BuLi, is a highly reactive organolithium compound. It is a strong base and a powerful nucleophile, widely used in organic synthesis. Its chemical formula is (CH3)3CLi. Due to its strong basicity, it is capable of deprotonating a wide range of organic substrates, including weakly acidic protons. This property makes it useful for generating carbanions, which can then undergo further reactions such as alkylation or addition to carbonyl compounds.

The reactivity of tert-butyllithium necessitates careful handling. It is typically supplied as a solution in hydrocarbon solvents like hexane or pentane, and it must be stored under an inert atmosphere, such as nitrogen or argon, to prevent reaction with air and moisture. Its reaction with water is vigorous and exothermic, producing tert-butanol and lithium hydroxide. Similarly, it reacts readily with oxygen, leading to potential ignition.

In organic synthesis, tert-butyllithium is employed in various transformations. It is frequently used for metal-halogen exchange reactions, where it can replace a halogen atom on an organic molecule with a lithium atom, generating a new organolithium species. It is also utilized in directed ortho-metallation reactions, where it can selectively deprotonate a position ortho to a directing group on an aromatic ring. Its high reactivity makes it a valuable tool for chemists seeking to construct complex organic molecules.