|This science article is a stub. You can help Wikiquote by expanding it.|
- Lithium aluminum hydride (LAH) is a powerful reducing agent but is not very chemoselective. It must be used in nonprotic solvents such as Et2O or THF; and one is advised to determine its concentration by hydrolysis. … The reduction of esters to primary alcohols and the reduction of amides to amines requires two hydrides, whereas reduction of carboxylic acids to primary alcohols consumes three hydrides. … The reactivity of LAH may be tempered by the addition of dialkyl amines. … The reactivity and selectivity of LAH can be modified by replacing three of its hydrides with t-brxtoxy or ethoxy groups. … Sodium bis(2-methoxyethoxy)aluminum hydride, or Red-Al, is a versatile, commercially available reducing agent. It is thermally more stable than LAH and may be used in aromatic hydrocarbon as well as in ether solvents. Overall, the reducing properties of Red-Al are similar to those of LAH (reductions of aldehydes, ketones, esters, etc.).
- George S. Zweifel and Michael H. Nantz, Modern Organic Synthesis (2006), Ch. 4 : Functional Group Transformations: Oxidation and Reduction.