Acyl Reductive Addition
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Table of Reduction of Carboxylic Acid Derivatives

Additions and Substitutions

(may require a hydronium workup)

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Net Substitutions

Net Additions
Derivative (+3) Ketone (+2) Aldehyde (+1) Alcohol (-1) Amine (-1)
Carboxylic Acid     LiAlH4, 1°  
Carboxylate Salt     LiAlH4, 1°  
Primary Amide   [(CH3)2CHCH2]2AlH   LiAlH4, 1°
Secondary Amide   [(CH3)2CHCH2]2AlH   LiAlH4, 2°
Tertiary Amide   [(CH3)2CHCH2]2AlH   LiAlH4, 3°
Nitrile R-Mg++-X or R-+Li [(CH3)2CHCH2]2AlH   LiAlH4, 1° or H2, transition metal catalysis
Ester (not alkyl formate)   [(CH3)2CHCH2]2AlH LiAlH4, 1° or

2R-Mg++-X, 3°

  
Anhydride     LiAlH4, 1°  
Acyl Halide R2Cu-Li+ LiAl[OC(CH3)3]3H LiAlH4, 1°  

 

 

 

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Thursday, August 05, 2010 20:18