Z-Selective Wittig Reaction

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}

 

The first step of the Z-selective Wittig reaction
is the production of the syn oxaphosphetane via a highly puckered transition state.

The second stage is the decomposition of the oxaphosphetane intermediate which decomposes via a concerted transition state to form the Z alkene and the phosphine oxide.

Back to Wittig Summary

R. Robiette, J. Richardson, V. K. Aggarwal and J. N. Harvey, J. Am. Chem. Soc., 2006, 128, 2394–2409.