Organic Chemistry Portal



Base-Mediated Cascade Rearrangements of Aryl-Substituted Diallyl Ethers

Jolene P. Reid, Catherine A. McAdam, Adam J. S. Johnston, Matthew N. Grayson, Jonathan M. Goodman and Matthew J. Cook*

*School of Chemistry and Chemical Engineering, Queen's University Belfast, Belfast BT9 5AG, Northern Ireland, United Kingdom, Email:

J. P. Reid, C. A. McAdam, A. J. S. Johnston, M. N. Grayson, J. M. Goodman, M. J. Cook, J. Org. Chem., 2015, 80, 1472-1498.

DOI: 10.1021/jo502403n






Two base-mediated cascade rearrangement reactions of diallyl ethers lead to selective [2,3]-Wittig-oxy-Cope and isomerization-Claisen rearrangements. Both diaryl and arylsilyl-substituted 1,3-substituted propenyl substrates were examined, and each exhibits unique reactivity and different reaction pathways. The role of the base and solvent was key to the reactivity and selectivity observed.

see article for more examples

Key Words

[2,3]-Wittig Rearrangement, Oxy-Cope Rearrangement, Claisen Rearrangement

ID: J42-Y2015