In one adaptation called a SN2' reduction a formal organic reduction on an allyl group containing a good leaving group is accompanied by a rearrangement. One example of such reaction is found as part of a Taxol total synthesis (ring C):
The hydride is lithium aluminium hydride and the leaving group a phosphonium salt. The product contains a new exocyclic double bond. Only when the cyclohexane ring is properly substituted will the proton add in a trans position with respect to the adjacent methyl group. A conceptually related reaction is the Whiting reaction forming dienes.
Read more about this topic: Allylic Rearrangement
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