Mitsunobu Reaction Stage 3

NOTE: Important charges and non-bonding electrons are shown throughout the animation except during the transition state phase.

^{Click the structures and reaction black arrows in sequence to view the 3D models and animations respectively}

Due to the strong affinity between oxygen and phosphorous, the lone pair attacks the phosphonium cation leaving an amide anion. The amide anion then removes the acidic proton from the oxyphosphonium ion to form the product.

Stage 4 of Mitsunobu

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T. Y. S. But and P. Toy, Chem. - An Asian J., 2007, 2, 1340–1355.