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- Diisobutylaluminum hydride (DIBAL-H) can be obtained commercially neat or in hydrocarbon solvents. Reductions with DIBAL-H must be carried out in the absence of air and moisture. DIBAL-H is a very versatile reagent for the selective reduction of appropriately substituted esters or nitriles to the corresponding aldehydes and for the reduction of lactones to lactols.… In contrast to LAH reductions of esters, nitriles and lactones, where two hydrides are utilized, reductions of these compounds by DIBAL-H at low temperature can be stopped after the transfer of one hydride to the carbonyl carbon. … The reduction of esters to aldehydes generally works best when alkoxy or amino functionality is in close proximity to the ester group …
Treatment of nitriles with one equivalent of DIBAL-H at -78℃ followed by hydrolytic workup affords the corresponding aldehydes. Reduction of nitriles with two equivalents of DIBAL-H produces, after hydrolytic workup, the corresponding primary amines. DIBAL-H is the reducing agent of choice for regioselective reduction of α,β-unsaturated esters to allylic alcohols.
- George S. Zweifel and Michael H. Nantz, Modern Organic Synthesis (2006), Ch. 4 : Functional Group Transformations: Oxidation and Reduction