Double bond geometry

Stereospecific Peterson reaction (Base elimination - Diastereoisomer 1)

Background Colour:

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

In a base-promoted Peterson reaction the hydroxy group is deprotonated, and the oxyanion attacks the silicon atom intramolecularly. Elimination takes place via a syn-periplanar transition state. This is because the oxygen and the silicon are now bound together and it is the strength of this bond that drives the elimination forward. As was shown previously, the acid-promoted Peterson reaction of this diastereoisomer gives predominantly the E-alkene, whereas the base-promoted Peterson reaction produces the more sterically demanding Z-alkene.

Back to previous page

 

 

689