Abstract The mitsunobu reaction, discovered in 1967, involves the stereospecific reaction of an alcohol and a carboxylic acid in the presence of triphenylphosphine and diethyl azodicarboxylate (DEAD) to give an ester. This paper provides an overview of this chemical reaction and presents explanations via numerous diagrams and figures.
From the Paper "In 1976, it was found that the formation of nitriles is also easily reached when cyanide is used as a nucleophile under Mitsunobu conditions.10 Recently, however, acetone cyanohydrin has been used as a source of hydrogen cyanide for this reaction (see figure 7). With a comparable yield and a less toxic reagent, acetone cyanohydrin is a suitable replacement for HCN.11 In this system, similar to other Mitsunobu systems, sterically hindered secondary alcohols tend to give poor yields."
