Diethyl diazodicarboxylate DEAD

Scheme 3.23 The Mitsunobu reaction with fluorous condensation reagents [24] enables the simple purification of the reaction product and recycling of the reagents TPP (49) and DEAD (52). ( TPP = fluorous triphenylphosphine TPPO = fluorous triphenylphosphine oxide DEAD = fluorous diethyl diazodicarboxylate DCEH = fluorous dicarboxyethoxyhydrazine).

Sn2 inversion of an alcohol by a nucleophile using disubstituted azodicarboxylates (originally, diethyl diazodicarboxylate, or DEAD) and trisubstituted phosphines (originally, triphenylphosphine). 

The overall acceptance of hydrogen by a reducing reagent is demonstrated by item 10 of Table 8.5. Here, the diethyl ester of diazodicarboxylic acid (diethyl azodi-carboxylate [DEAD]) serves to oxidize 1-phenylpropanol to phenylpropanone while it is reduced to diethyl hydrazo-dicarboxylate in the process. Although the details are sketchy, a possible pathway is shown in Scheme 8.7. 

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