Allylic rearrangement

What is allylic rearrangement?

An allylic rearrangement refers to the movement of a C=C double bond in a three-carbon (allylic) system when exposed to nucleophiles under SN1 conditions. Alternatively, this rearrangement can also occur under SN2 conditions when nucleophilic attack takes place at the γ-carbon.

Allylic rearrangement - reaction scheme
Allylic rearrangement

References

Claisen, L. (1912), Über Umlagerung von Phenol-allyläthern in C-Allyl-phenole. [On rearrangement of phenol-allyl ethers to C-allyl phenols.] Ber. Dtsch. Chem. Ges., 45: 3157-3166. https://doi.org/10.1002/cber.19120450348

Shares