Conversion of acid chlorides to aldehydes using LiAlH(O-tBu)3
Description: Addition of the bulky reducing agent lithium tri-t-butoxy aluminum hydride [LiAlH(O-tBu)3] to acid chlorides results in the formation of aldehydes.
Notes: The nucleophile here is the hydride ion, which adds once to the acid halide, resulting in the aldehyde.
Notes: The byproduct of these reactions are LiCl and Al(O-t-Bu)3
Mechanisms: Addition of the hydride to the acid chloride (Step 1, arrows A and B) results in a tetrahedral intermediate, which undergoes elimination of chloride ion (Step 2, arrows C and D) to give the neutral aldehyde.