Esters and amides arenotreduced by NaBH4under normal conditions. (They can be reduced by lithium aluminum hydride (LiAlH4) however). NaBH4is also used in the demercuration step of oxymercuration-demercuration. Notes Related Articles Lithium Aluminum Hydride (LiAlH4) For Reduction of Carboxylic Acid...
So I thought let’s look at the mechanism of ester with LiAlH4, which goes as followed: What I see is that there are two reduction processes to receive the final product. While the reduction of an ketone only has one. Does this explain the difference in reactivity? So why isn’t it ...
Enamine chemistry--XXV* 1:: Reduction of enaminones by LiAlH4 and NaBH4. Synthesis of [alpha],[beta]-unsaturated aldehydesdoi:10.1016/0040-4020(82)80183-xS. CarlssonS.-O. Lawesson