tBuO

tBuO is a shorthand used in organic chemistry to denote tert-butoxy species. It can refer to the tert-butoxy group attached to an oxygen atom (ROtBu), the tert-butoxide anion (t-BuO−), or the tert-butoxy radical (t-BuO•), depending on the chemical context.

Common forms and roles include the tert-butoxide anion and its salts, such as potassium tert-butoxide (KOtBu) and sodium tert-butoxide (NaOtBu). These are bulky, highly basic, and generally non-nucleophilic bases that are widely used to deprotonate weak acids and to promote E2 eliminations and enolate formation in organic synthesis. The corresponding tert-butyl ethers (ROtBu) arise when the tert-butoxy group is bound to an alkyl or aryl fragment; these ethers are frequently used as protective groups for alcohols because ROtBu can be introduced under mild conditions and later removed under acidic or strong conditions.

In radical chemistry, t-BuO• (tert-butoxy radical) plays a role as an intermediate in various radical processes. It is typically generated by homolysis of tert-butyl hydroperoxide (t-BuOOH) or related precursors and can participate in hydrogen abstraction and chain-transfer reactions.

Preparation and handling: tert-butoxide bases are commonly prepared by deprotonating tert-butanol with a strong base, such as sodium hydride or metallic alkali to give NaOtBu or KOtBu, often in inert solvents. They are moisture- and air-sensitive and can be highly reactive with acids and water, requiring careful storage and handling.

Safety: tBuO-containing reagents are strong bases and irritants. They may react vigorously with water and oxidizers; appropriate personal protective equipment and proper ventilation are essential. Storage should minimize exposure to moisture and incompatible reagents.