Lithium diisopropylamide

• Diisopropylamine lithium salt
• LDA

Spontaneously combustible, moisture- sensitive solid

Fixed ( but usually in solution)

0.86 g · cm -3 ( 25 ° C)

Soluble in hexane

Risk

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Lithium diisopropylamide (LDA ), the lithium salt of diisopropylamine. It is a strong base, which is often used in organic chemistry for the deprotonation of CH-acidic compounds. Due to the steric hindrance by the bulky isopropyl LDA is not very nucleophilic. The pKa of the conjugate acid is 40 Thus, it is possible to deprotonate also weak CH- acidic compounds such as carbonyl compounds in the α - position, and this thereby converted into enolates. Commercial LDA is usually available as a solution in diethyl ether or THF. In these solutions it forms dimeric structures.

Production

LDA may be prepared from diisopropylamine with organolithium compounds such as phenyllithium or butyllithium. A cheaper way is the reaction of elemental lithium diisopropylamine in the presence of styrene.